Sweet Polly Oliver

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"As sweet Polly Oliver lay musing in bed,
A sudden strange fancy came into her head.
Nor father nor mother shall make me false prove:
I'll 'list as a soldier and follow my love.

So early next morning she softly arose,
and dressed herself up in her dead brother's clothes,
She cut her hair close, and she stained her face brown,
And went for a soldier to fair London town."

— English Folk Song

A female character dresses up as a man to accomplish some end. Often becomes a variant of the Jackie Robinson Story. The sports version is especially popular in children's media, since it allows for an Anviliciously contemptuous boys' team for the heroine to win over with her talents.

Named for the old, old folk song "Sweet Polly Oliver" (quoted above), in which a woman disguises herself as a man so she can join the army and follow her soldier lover. However, the trope predates the name, going back further to The Ballad of Mulan, a 5th-6th century AD Chinese legend. And of course, women disguising themselves as men in order to join the military has happened time and again throughout history, for any number of reasons — a deeply held desire to do so, a living in times when there was no other way to support herself, even getting away from a terrible situation at home.

A Transgender man might be mistaken for a Sweet Polly Oliver. It can be difficult to tell if a Real Life Sweet Polly Oliver was actually trans if they never made a statement on their own gender.

If a girl dresses like that all the time, she might be a Wholesome Crossdresser. Sometimes the audience (or a character) doesn't know this at first, and is surprised to find out Samus Is a Girl.

Contrast with Harmless Lady Disguise, Moustache de Plume, and Disguised in Drag; is a type of She Is the King (Type 1, to be specific). Some men may subconsciously see through this, and become Sweet on Polly Oliver. Since, in most cultures, she needs a new name, may occasion a Meaningful Rename. Not to be confused with Bifauxnen. If employing this trope allows a female character to be the first of her gender to achieve something, she's Breaking the Glass Ceiling (or sneaking past it, anyway).

Many times when this is done in film and TV, the actress playing the crossdressing character rarely does a convincing job (see Hollywood Homely), requiring Suspension of Disbelief on the part of the audience that the other characters encountering her really believe she is male. On the other hand, quite a few women really did get away with this surprisingly easily in the past, which The Folklore of Discworld phrases as:

in an age before unisex fashions, trousers meant 'man' and skirts meant 'woman'. Trousers plus high-pitched voice meant 'young man'. People didn't expect anything else, and saw what they expected to see.

To make it easier for the audience to believe that Sweet Polly Oliver passes for male, she'll often be tall and lack curves. If she begins crossdressing at a young age, she might worry about it being harder to pass when she goes through puberty.

As a type of Weirdness Censor, the human mind will simply ignore small details that could give the ruse away, once it has classified a person as either male or female. And in societies in which male and female gender roles are clearly separated with no room for overlaps, this effect would be even stronger, as the idea of meeting a cross-dresser would be even more inconceivable than it is today.

You can listen to the full version of the song here.

Examples:

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Anime & Manga

"Pierre", actually Valerie, is a villainous version on Agent Aika, whom the titular character falls for.
Mikusa from Arata: The Legend must disguise herself as a male of the Himezoku for reasons she does not disclose to Kotoha. She's eventually forced to reveal to Hinohara that it is because she's not even truly of the Himezoku.
Done by Yelena, one of the anti-Marleyan volunteers in Attack on Titan, who dons a male Marleyan military uniform and fake beard as a disguise. This is because Yelena's been assumed dead by said military and was a soldier who was on a ship that got sent to Paradis Island and never returned. Her disguise is recognised by Pieck, the Cart Titan, but Pieck doesn't initially remember who she is, just that she'd seen Yelena somewhere before. Pieck was in charge of overseeing the ship Yelena was on before it left for Paradis.
Basara: The story takes place in a future Japan, reduced to a barren desert by a catastrophe at the end of the 21st century. The main character is Sarasa, a girl whose twin brother, Tatara, is prophesied to be the "child of destiny" who will bring back the country's independence and stop the tyrannical rule of the Empire, namely the Red King. When Tatara is killed, Sarasa pretends to be him in order to keep the downtrodden from losing hope.
Casca from Berserk is an interesting example as she both archives this trope and subverts it at the same time. When she was first introduced she's armored enough that the protagonist Guts thought he was fighting a man, until he knocked her helmet off. Princess Charlotte also assumed Casca was a man when she first met her and was surprised to learn otherwise when meeting her again. On the other hand, most enemy soldiers and Apostles aren't fooled for a second and easily recognize Casca as a woman, and try their best to rip her armor off and violate her.
Candy White-Andree in Candy♡Candy is grounded during a school festival, but a friend of hers sneaks her a box with two outfits: a female gown and a male disguise, both with matching wigs. (A gift from her Mysterious Protector, who had sent it before she was punished.) She uses them to sneak away and have fun without being caught by the school staff, alternating between the girly girl facade and the boyish one. Hilarity Ensues.
An early episode of Cardcaptor Sakura has a minor character named Yuuki dress up like a boy while she tries to remove a card's influence from her Disappeared Dad's painting. Sakura doesn't notice her gender until the girl's hat falls off and reveals her long hair.
The heroine of Castle in the Sky dresses as a boy to evade capture. The disguise doesn't fly for long.
A Girl of the Week in City Hunter disguises herself as a man before requesting help from Ryo for her own safety — against the criminal who would want her dead and from Ryo alike.
A ChocoMimi extra had Mikami think Mumu is this. He asks him about this in his own weird way.
Mikami: Only a son...could be the heir. But no boy was born. Just three sad sisters. So the oldest cut her hair...and lived as a man. Is that your story, Mumu?
Mumu: Nope! I was born a boy.
In Classi9, Ren has to pass as a boy named Rentarou to keep studying music in Melite. Except for Mozart, who led her there and ended up becoming her Secret-Keeper, no one is allowed to know about her gender, or they will both be expelled.
In Claymore, Clare disguises herself as a man for a time in order to travel under the radar, even using her limited Shapeshifting abilities to elongate her vocal cords and deepen her voice.
In Cynthia the Mission Shii, the male 'protection' personality of the busty and beautiful Kanae manages to pull this off with a specific jacket designed to minimize her bust. It doesn't help that Shii acts very much like a man.
In Girl Got Game, Kyo is forced/convinced by her father to pretend to be a boy so she can fulfill his dreams of playing basketball. She also lives in the boy's dorm with a boy she hates who she of course ends up falling for. This series is pretty much a parody of the genre. Similar to the example in Mulan, Kyo has many severe male stereotypes she tries to emulate with little success. She ends up adapting, however, and wonders if she can ever go back to being feminine. Her roommate also has an interesting way of coping once he discovers her true gender.
Subverted in Girls Saurus, where all the other students at the boys' school Tsubasa goes to are convinced he's actually a girl pretending to be a boy, even though he isn't... Except for tough guy Arahata, who refutes the idea as ridiculous. "What do you think this is, a shoujo manga?" Of course, then when he goes to confront Tsubasa on the matter, he's utterly convinced that he's a girl after one look at him, too. He also gets molested by men on the train to school.
Michel Volban of Glass Fleet is a noblewoman who assumed her older brother's identity and his role as leader of La Résistance.
In GO-GO Tamagotchi! episode 40, Himespetchi wants to follow her crush Mametchi when he gets to audition in a television show. To do this, she masquerades as a boy named Himeboytchi to get a role as a male lead character.
Helmut Marx Von Babel of the Baselland Military Academy's cavalry divsion in Gunka No Baltzar. Her sex isn't discovered until the protagonist forces her to strip to remove the leeches that got all over her when she forded a river.
Mizuki Ashiya from Hana-Kimi who dresses up as a guy to get together with her favourite high jumper, Sano. They get close enough that people mistake them for Yaoi Guys and even Shuichi (the loud guy...) starts liking her thinking she's a guy, leading to some odd situations to say the least.
Itsuki Myoudouin from HeartCatch Pretty Cure!, taking her big brother Satsuki's role due to the aforementioned man having a weak heart. For added "hilarity", Satsuki is also a case of Dude Looks Like a Lady. He got better after a risky treatment, and Itsuki was able to resume being a girl by the end of the show. It should be noted that while Itsuki is mistaken for a boy several times in the series, pretty much everyone in the school knows she's a girl. Not that it matters much ...
Alicia "Jeudi" Brandel from Honoo no Alpen Rose must do this in the manga to go to Austria unnoticed, calling herself "Julian", so she can escape from her Stalker with a Crush and find the people who can tell her who she truly is. She does it so well that two girls find her boy self "handsome", and one of them (Liesl) is quite infatuated with "him" too... And she may have been a bit infatuated wuith Jeudi after finding out, too. Sadly, it was cut from the anime.
Kei from IRIA: Zeiram the Animation looks like a tough-talking street rat of a boy (it's meant to make Kei look tough) until Fujikuro's sharp nose picked up the truth about her. This makes things interesting since Kei is also attracted to Iria, though most figure it to be Iria being someone to look up to, much as how Iria looked up to her brother Gren in her youth.
Anne, a runaway girl in JoJo's Bizarre Adventure: Stardust Crusaders, tries to pass herself off as a runaway boy to sneak onto a boat and travel the world, believing that it would be impossible to pull off such a disguise once she started to physically mature.
In Kaze Hikaru, the main character Tominaga Sei disguises herself as a male swordsman after the murder of her family to avenge herself on their killers, and ends up joining The Shinsengumi.
The Yuri Genre oneshot Liar and the Ferris Wheel is about a girl that falls in love at first sight with another girl. She pretends to be a boy to go on a date with her. The other girl knew the entire time though.
Subverted in Ludwig Revolution. When we see a flashback of a princess being outcast and then flash forward to Petronella calling Julius "Julianna", this is where your mind goes, right? Turns out the young Princess Julianna is a trans woman. Maybe.
Akira in My-HiME disguises herself as a man. In the German version of the dub, she's even given a man's voice (and not even a woman playing a man's voice, at that), as the production company was not aware "he" was actually female...
Shizu, Mariya's twin sister in Maria†Holic is doing the exact opposite of her brother by playing out this trope. None of her antics over at Mihoshi no Mori Boys' School have been seen, but this is especially troubling for Shizu since she Does Not Like Men.
The manga adaptation of Mega Man 6 has the titular protagonist knock off Centaur Man's helmet, revealing her long flowing hair. Turns out that she disguised herself as a male.
Irene Adler from Moriarty the Patriot disguises herself as a man on two separate occasions. The first is when she pretends to be the King of Bohemia to hire Sherlock's services and rope him into her schemes. Then, she does so again when meeting Albert at a masquerade. Eventually, Irene decides to become a man full-time, and the new identity? Bond... James Bond.
In Naruto the male daimyo Sagi is eventually revealed to in fact be his twin sister Toki. After her brother's mysterious death, she swore to avenge him; to do so, she assumed the role of her brother and claimed the body that was interred was herself. Once her family's enemy was revealed and eliminated she revealed the truth of her deception to the people and continued in her role as daimyo.
Kiri in the manga Never Give Up poses as a male model so she can stay close to her neighbor and love interest, Tohya. It helps a lot that Kiri already looked just like her dad, who was a model too.
Nononono: The whole premise is Nono Nonomiya passing of as her (deceased) twin brother Yuuta, in order to make it into the ski jump Olympics and win a gold medal. She does this since women aren't allowed to compete professionally in that event.
Nozomu Nozomi is about the evolution of a middle school boy from Wholesome Crossdresser to Sweet Polly Oliver under the influence of female puberty over the course of a year following an inexplicable Gender Bender. Nozomu starts out identifying as a boy who likes to dress as a girl in private but eventually ends up identifying as a girl who is forced to dress as a boy in public who feels she must maintain the pretense because she's afraid of the consequences of revealing her true gender.
Briefly becomes very common during the earliest (chronological) arc of Ōoku: The Inner Chambers as numerous heads of noble houses, seeing a gendercide plague kill off their sons and nephews, mask the absence of male heirs by dressing their daughters in drag and bringing them to public events like annual oaths of fealty to the Shogun. Then one year the screen hiding the elusive Shogun Iemitsu is raised and a young woman (complete with a kimono, makeup, and a wig to mask how short she had been keeping her own hair) commands all present to behold their ruler.
Otogi Zoshi: Hikaru disguises herself as her brother, because he is sick and later dead. The series loses a bit of charm when she drops the disguise.
One of the major plot points of Ouran High School Host Club, with the twist that Haruhi wasn't trying to pass as a boy, she was just wearing castoff men's clothing because she couldn't afford her school's expensive uniform, and didn't care enough to correct the members of the Host Club when they jumped to conclusions about her gender. A good half the comedy of the series springs from the boys of the Host Club running themselves ragged to keep Haruhi's gender a secret from the rest of the school, while Haruhi herself continues to not care.
Yellow successfully passed herself off as a boy for the bulk of Pokémon Adventures' Yellow chapter. Red (and the cast introduced in the GSC Arc) didn't know Yellow was a girl until the end of the GSC Arc. Most everyone else already knew by the end of the Yellow Arc.
Ranma ½:
- Akane disguises herself as a boy in order to battle the Yamata no Orochi without being eaten as the beast loves the taste of women.
- Ranma's Unlucky Childhood Friend Ukyou "gave up" her femininity and passed herself off as a male (to the point of attending a boys-only school) after Genma and Ranma ran out on her marriage arrangement. Once her ruse is discovered, however, she quickly abandons the pose and crosses over into Wholesome Crossdresser territory (but only at school, her "civilian clothes" are all feminine even if she still acts boyishly); later that season (in the anime only) she even abandons that once, causing all of the boys at Furinkan High to wonder who the "cute girl" is. She wears the girl's uniform at least once after that (and lampshades it, naturally). She also attracts some cross-dressers of the opposite sex (other than Ranma), namely Tsubasa and Konatsu.
- Subverted when Ranma is locked in his female form by Cologne and he has to resort to disguising as a boy in order to fight Mousse. Disguise doesn't help him with his inferior feminine physique, though.
- Inverted by Ranma on occasion, who uses his girl half to get snacks. Both because it's easier to score freebies as a cute girl, and because it would be unmanly for a boy to pig out on sweets.
Juliet Fiamatta Asto Capulet in Romeo × Juliet dresses as a boy named Odin to disguise her connection to the Capulet family line, as the last surviving member is known to be female. After Juliet learns of her heritage, she's allowed to wear dresses and let her hair down when she's in the Capulet headquarters and away from intruders, and she takes it on stride. (Then again, when she pulled a Recursive Crossdressing stunt at the start, she did like wearing a fancy gown.) And once Juliet's identity is revealed to the public and everyone knows who she truly is, she just doesn't bother with disguises anymore and wears either simple dresses or tomboyish clothes depending on the situation.
The incredibly Bifauxnen Oscar of The Rose of Versailles dresses as a man for her day job of commander of the Royal Guard. The rest of the time, she just does it because her father reared her as a boy.
Sailor Moon:
- Done in the Sailor Moon manga by Minako. She uses the Crescent Compact to transform into a male Mugen Gakuen student so she can slip into the school and watch the concert of idol Mimi Hanyuu, who is secretly Mimette. She also does this at least once in the prequel, Codename: Sailor V.
- In the manga, both Nephrite and Sailor Moon did this—Nephrite as a ghostly bride, and Sailor Moon as the ghostly bride's groom.
- Sailor Moon also disguises herself as a reporter in the first-season anime episode "Cruise Blues". If that isn't obvious enough, look at how short her hair is in this disguise!
Tsukiko from Samurai High School switches places with her Half-Identical Twin brother Kou to enter said high school and become Supreme Commander of Japan. It helps that they both are adept at the opposite gender roles.
Shishunki To Danshikou To Nakano Kun (Puberty, an All Boys School!? and Nakano-kun): The premise of the story is an exaggeration of the trope. Hajime Nakano is sent to an all-boys school because his mother feels (accurately) that he's too girl-crazy. What Nakano does not know is that literally every single student in his school except for him is a girl posing as a boy for, quote, "unavoidable reasons". Adding to the exaggeration is that the girls don't realize this, either. Every girl thinks they're the only one in disguise and everyone else is actually a boy.
Subverted in Shugo Chara!: When Nadeshiko's "twin brother" Nagihiko shows up in one episode, it seems painfully obvious, that it is her in disguise... until it is revealed that actually EVERYTHING ELSE was the disguise and Nagihiko is Nadeshiko's REAL identity.
Kyouko from Skip Beat! does this when she is challenged to act as the challenger's son.
The Three Musketeers: This turns out to be what Aramis is doing, having disguised herself as male so that she could be a musketeer.
In Tokyo Ghoul :Re, it is eventually revealed that Kanae von Rosewald is actually a woman that has spent the last decade living as a man. She adopted her male identity because of the deaths of her brothers, believing it was her responsibility to carry on the family legacy in their stead. Though it seems to be an Open Secret, the man she loves is oblivious and she persists in hiding it from him. Just before her death, she confesses her true feelings and Shuu finally calls her by her real name, Karren. She sacrifices herself to save him, and thinks how painful it was to live that way and how happy she is to be able to die as herself.
Part of the backstory for Override of Transformers: Cybertron was that she somehow disguised herself as a boy to enter the great race for planet leadership. The weird bit, aside from the concept of a crossdressing robot, is that Override is pretty damn androgynous anyway and is a male in the original Japanese.
Wolfsmund: The first chapter focuses on Lise, a Fallen Princess who has to disguise herself as her sole remaining knight Georg's squire to avoid detection, as she is wanted for being the daughter of a recently executed rebel leader. Too bad for both of them that Wolfram finds out.
In The World is Still Beautiful for a while starting from Chapter 31, Nike goes under disguise as "Vice Captain Kanaris Micaine" of Livius' army to pretend to be Luna's lover so they can stop her unwanted arranged marriage to Marquis Fortis. It fools everyone but him, so it turns out.
Yu-Gi-Oh! GX: Rei Saotome pretended to be a boy in her first appearance. She's found out when she loses her hat and this reveals her long hair.
Yuureitou: Subverted. Upon learning that he's the woman they've been looking for, Taichi initially believes that Tetsuo is disguised as a man to avoid being arrested for killing his adopted mother. That's not it. Tetsuo is a Transgender man and the murder was due to his mother not accepting that. It takes a while for Taichi to understand this, but he eventually comes to terms with it and realizes he loves Tetsuo even as a man.
Leo in the manga Dansou no Partner dresses up as a male, which the MC found out on the first chapter.
The entire concept of the manga The Reward For Keeping Quiet Was Sex With Girls Dressed As Men revolves around the MC finding out two students in his school, Kay & Akira, are females secretly cross-dressing as males.

Audio Plays

Big Finish Doctor Who: In Storm Warning, Edwardian adventuress Charlotte 'Charlie' Pollard gets a junior steward named Simon Murchford drunk, leaves him passed out in the tavern stables, and steals his papers and his kitbag in order to take his place on the maiden voyage of the airship R101. Her masquerade does not last long, but what trips her up is not her disguise, but her inability to keep track of her assumed accent.

Comic Books

Marvel 1602: Carlos Javier has a page named John Grey. Scott Somerisle is insanely jealous of "John"'s friendship with Angel, much to the latter's confusion. When Scott finds out that Angel honestly didn't know that "John" was female, he apologizes... only to be told that Angel was, in fact, in love with Jean's boy-persona.
Supergirl:
- In Adventure Comics #384: "The Heroine Haters", Supergirl meets Volar, the female hero of planet Torma, who dresses up as a male because her planet's misogynist society wouldn't accept to be protected by a woman.
- "The Unknown Legionnaire": Unknown Boy, a masked super-being who shows up all of sudden to help the Legion of Super-Heros turns out to be an amnesiac Supergirl disguised as a male.
"Jack", in the Deathwatch comic strip by Paul Cornell, is quite clearly a girl wearing a false moustache to work as an actor. And, inevitably, ends up playing Helen of Troy in Faust.
Subverted in Demon Knights with the Shining Knight (who is a Sweet Polly Oliver in some other versions as well). Her costume looks convincing to the reader (due to the fact that she's very flat-chested) but fools no one in-universe. And then played with further when it turns out assuming she's a woman is wrong as well; she's non-binary in some way (nobody in the setting has the right terminology; she describes herself as "both").
Disney Kingdoms: In "Big Thunder Mountain Railroad", Abigail disguises herself as a man to infiltrate the mine.
The Spanish comic magazine El Jueves had a story, Emiliao where a girl, Emilia, pretended to a boy to do the mandatory conscription in the Army and be with her boyfriend.
In Justice League Task Force, there's Mystek, who wore a very masculine armored suit. One of her teammates, Triumph, found out the truth on a trip through space. Mystek, who got claustrophobic when in costume, hid in the bathroom to take it off. Triumph eventually demanded that she come out, having had enough time to "drain the weasel". He opened the door, saw the indignant lady inside, walked back to his seat in a daze, and whispered, "Mystek has no weasel."
In Legion of Super-Heroes, Lightning Lass made her first appearance pretending (rather inexplicably) to be her dead twin brother, the Legionnaire Lightning Lad. The deception was exposed when Sun Boy noticed that she didn't have an Adam's apple.
Echo from New Avengers, who posed as a male hero named Ronin in order to infiltrate the Tokyo underworld. It was an ingenious move, especially when you consider that if gangsters were looking for a male hero with a very Japanese-sounding name, a small Latina woman would be the last person they'd suspect.
Agnès de Roselande/Isabeau de Marnaye in the Francois Bourgeon's historical series Les Passagers Du Vent.
In Prince of Persia: The Graphic Novel, when Shirin leaves the city of Marv in search of La Résistance, she cuts her hair and masquerades as a boy named Shapur.
The Princess and the Grilled Cheese Sandwich: Cam has to pass herself off as a man because women cannot inherit at all in this setting. In fact, the whole thing was her father's idea so she would not be left destitute upon his death.
The Sandman (1989): Jim the "cabin boy" in Hob's Leviathan is actually a girl named Peggy.
A comic strip in the They Think It's All Over Christmas Annual featured a girl who disguised herself as a boy to join her local football team, because they were so useless. In a rather mean-spirited subversion of how this sort of story is supposed to go, not only did she turn out to be a poor footballer, but the rest of the the team were all secretly girls as well, which — we were expressly told — explained why they were rubbish.
In one Weird War Stories, a drummer boy being held in a American Civil War prison camp turns out to be a girl, leading to a Sweet on Polly Oliver'' situation. And then zombies attack...
As a young girl, Martha Washington in Give Me Liberty habitually passes herself off as a boy to avoid being sexually assaulted. She then gets grabbed by someone looking for young boys.
W.I.T.C.H.: Vicky and Irma in the World Cup/Football Special. They posed as boys so they could play on the football team.
Cornelia: What should we call you? Irmo?
Wizards of Mickey: Trudy van Tubb is introduced this way in The New World, having dressed up as a man in order to join Pete's pirate crew.
Wonder Woman (1942):
- Byrna Brilyant's Blue Snowman suit makes her look like an older overweight gentleman and thus acts as a very thorough disguise. Modern portrayals give the character an Ambiguous Gender Identity, or directly say they're gender-fluid.
- Maru binds her chest, wears baggy clothes and a masculine mask in her Dr. Poison disguise.
- Hypnota disguises themself as a man for their stage shows, but has an Ambiguous Gender Identity as their identical twin sister usually refers to them with male pronouns, they themselves switch between male and female pronouns and after their sex is revealed they wear their mustache and goatee but do nothing to hide their female figure.

Fan Works

In Austraeoh, the stallion caravan guard Gold Plate turns out to be not so much a stallion at all; "he's" actually a mare called Gold Petals.
In Children of Time, Beth Lestrade dresses as a street boy out of necessity when in Victorian London, first to join Sherlock Holmes on a case, then for purely practical reasons when she and the Irregulars are on the run. To her amusement, her own ancestor falls for her disguise, though she later confides to Holmes that she was rather surprised it worked.
In Emergence, Ruby is chosen to be part of a mission in Syria dealing with ISIS terrorists because with her short hair, she can pass for a boy at a distance with the help of baggy clothes.
There's more than one Hetalia: Axis Powers fic out there that imagine the female Nations as being forced to do this out of necessity (i.e. avoid getting raped by their own soldiers), though this usually happens in historical-themed stories to stress the Values Dissonance.
Kindsar's Phenomenon reimagines Captain Kirk as this trope - whilst he uses male pronouns throughout, has undergone a reasonably substantial amount of surgery, and intends to keep the male body he finds himself in thanks to the Gender Bender until he eventually has to choose between the convenience of the aforementioned body and remaining bonded to Spock, who can't stay flipped without dying horribly and who is biologically incapable of bonding with another male no matter how much he might want to, he also admits to not really identifying as male, and only passed himself off as such because women can't become starship captains.
In The Lost Girl, Friendly is a variant of this, as she quickly forgets she ever was a girl.
In one Lucky Star fanfic, Misao is in a Secret Relationship with Ayano. She dresses up as a boy and pretends to be Ayano's "boyfriend" in public.
In Pretty Cure Perfume Preppy, Sasaki, when she was in the basketball team masquerading as her brother.
In The Red Monarch, Tatsuki does not actively try to hide her gender, but the short hair, baggy clothes - and presumably androgynous appearance - make everyone mistake her for a very cute boy at first.
The Rigel Black Chronicles is based on Harriett Potter pretending to be her cousin Archie in order to study at Hogwarts. The gender swap is secondary, though; Hogwarts doesn't discriminate by gender but by blood status, and her cousin is a Pureblood. Still, to make it work, she has to convincingly pretend to be a boy, gaining a reputation in the process for remarkable shyness about bare chests, and for sleeping in robes.
In Royal Ward Princess Diana mentions the time she dressed up as a man and went to a gay bar with Kenny Everett and Freddie Mercury.
In RWBY Alternate, Cordovin (which isn't her true name) enlisted in the military as a male because women are banned from her country's military. She spent decades working under her male disguise.
In Silencio, Lisa convinces Taylor to crossdress in costume to keep her identity secret. It works somewhat too well- 'Marceau' becomes quite the accidental ladies' man.
In Sixes and Sevens, Emily disguises herself as a young boy when the team sneak through Nazi-infested waters during Shadow of the Eagle.
In the Naruto story Spider Thread, Tomoe pretends to be a boy while traveling because she thinks it would be safer. The ruse continues long after it's necessity is gone.
In the Hamilton fanfic Sweet Polly Oliver and the Tomcat, Eliza Schuyler decides, at the age of five years old, to become her father's son, so that her family has someone to continue their legacy. In doing this, she was inspired by the trope namer, which her grandmother used to sing to her as a young girl.
A Thing of Vikings:
- Gudmund Hallvarsson is actually Heidrun Hallvarsdóttir, a woman who took up her father's sword and joined the Varangians when her brother decided to run away to Berk and become a blacksmith instead of a warrior. Her secret eventually comes out when she gets pregnant, but Sigurd manages to get the Empress to pardon her.
- Like in the movie she's from, Mulan disguises herself as a man named Ping for safety when she travels with Shang and the trio to the west. Unlike the movie, it's not to join the military, and Shang knows her identity from the start.
Cody in the Total Drama fanfic Total Lady Drama Island is made an offer by Chris after a clerical error puts him on the list of contestants for a version of the show with all-female contestants. If he pretends to be a girl and manages to win without being outed by another contestant then he'll win four times the prize money. He accepts.
Samn in Warriors Kingdoms: The Prophecy Begins is a girl masquerading as a boy. She wants to be a knight, but women aren't usually able to become knights.
In the The Hunger Games fic What's So Civil About War, Anyway?, Katniss joins the Union army by hiding as a boy called Kat. Somewhat subverted in that it does not take long for most people in her unit to learn her true identity, but they are cool with it, anyway. There is also a joke about another woman getting caught and sent back home.
In Wolf Cub girls weren't allowed to be on Quidditch teams during Harry's parents' schooldays due to prejudice, so Remus' half-werewolf sister dressed in a boys' uniform and called herself Tam O'Flahearty in order to participate in tryouts. She won a spot as Seeker, pushing Harry's father, who was also trying out into the vacant Chaser position.
- A similar premise is used in In Love of Quidditch where girls aren't allowed to fly at all because it isn't considered "ladylike." In this case, Harriet Potter goes to Hogwarts, which her twin brother Alexander was supposed to attend, as "Harry" Potter in hopes that she can play professionally someday, while her brother attends the no-Quidditch academically-oriented school their father was sending her to so he can become a curse-breaker.

Fairy Tales

In "Belle-Belle", Belle-Belle disguises herself as a male knight since her father is too old to fight for the king. Belle-Belle is even wooed by the lady-in-waiting Florida, who does not know that she is a woman.
In "Costanza / Costanzo", Costanza disguised herself to go into service because she could not get a suitable bridegroom of Royal Blood, only one of Blue Blood.
In The Discreet Princess, the titular character delivers her newborn nephews to their Evil Prince father while disguised as a doctor treating him after their last encounter.
Several Italian fairy tales have this, ranging from going to war, saving a prince dressed as a doctor, escaping from villains, or simply because they feel like it / a magic pony told 'em to. Examples: "Fantaghiro the Beautiful", "The Dragon and Enchanted Filly", "The First Sword and the Last Broom", "Wormwood", "The King of Spain and the English Milord", "The Great Narbone", "The Parrot", "The Canary Prince"...
In "The Girl Who Pretended to be a Boy" the youngest daughter of an emperor disguises herself as a boy and rescues a princess. The ending though indicates Fet-Fenurs may have been transgender all along, since he is happy to be transformed into a man.
In "The Lute Player", the queen dresses as a man to get safely to her husband.
The Icelandic fairy tale "The Story of King Odd" is about an elf queen who is forced by the circumstances to pose as a man in the human world.
In the Middle Eastern fairy tale The Story of the King, Hamed bin Bathara, and of the Fearless Girl, Princess Sherifa is astonished to hear that the king of the neighboring kingdom has banished all women and wants to find out for herself what's happening. Because of the whole "women are banished" thing, she disguises herself as a boy and quickly becomes the king's new best friend. The king starts to get uncomfortable when he can't figure out why he's attracted to his friend and tries a number of tests to see if his friend is secretly a woman. The princess passes each one and the king finally tries to trick her into undressing for a swim at the beach, at which point she jumps into the ocean and swims away. He only figures out she's a woman by seeing that she carved the truth into a door before leaving.
The Brothers Grimm fairy tale "The Twelve Huntsmen" (who are actually a princess and eleven female companions disguised as men).
The Russian fairy tale "Vasilisa the Priest's Daughter" is about a young woman who dresses like a boy, rides a horse, and shoots a gun (apparently just because she likes it). The king doesn't believe his servants when he's told the "young man" is a girl, and invites "him" to dinner, where he subjects her to several Secret Tests to figure out her gender. Finally, he invites the "young man" to take a bath with him, but he takes so long getting ready that she's finished and gone by the time he enters the bath.

Films — Animation

The Breadwinner has been compared to Mulan for its use of this trope. Due to the Taliban's strict rules about women Parvana has to cut her hair short and wear her dead brother's clothes to go out and take odd jobs to buy food for her family. Later on she meets with an old friend from school named Shauzia who is doing the same thing.
In Fireheart, Georgia is the daughter of a fire chief in 1930s New York, who dons a false moustache after being told girls can't be fire fighters.
Fa Mulan disguises herself as a man by making her hair shorter and wearing a soldier's outfit so that her disabled father won't have to go.
Parodied in The Pirates! In an Adventure with Scientists with the pirate named Surprisingly Curvaceous Pirate. No-one in the film seems to work this out, despite it being very obvious.

Films — Live-Action

A 1997 TV movie adaptation of 20,000 Leagues Under the Sea has Aronnax's Canon Foreigner daughter Sophie doing this to accompany him on the expedition, under the alias "Charlie Darwin".
Albert Nobbs: Albert and Hubert are both biologically female though living as men, with male clothing, for work. However, one or both could be transgender, it isn't clarified.
In the Whoopi Goldberg film The Associate, Laurel is a black woman trying to make it on Wall Street, and she creates a white male alter ego to pass off her business ideas as his. "Mr. Cutty" might not be a particularly handsome man, but Laurel puts in the work to look and sound like one, as she is coached by a Drag Queen friend and wears a latex mask and wig as part of her disguise.
In The Butchers, Jack the Ripper is really a beautiful woman disguised as a man via Latex Perfection.
In Carry On Jack, Sally steals Albert Poop-Decker's uniform and takes his place on the frigate Venus, while Albert finds himself pressganged onto the same ship as a common seaman.
The whole premise of a Canadian TV movie called The Challengers. Mackie is a young girl and she disguises herself as a boy to join a boys-only band who has a strict "no girls allowed" policy. She hides her long hair in a baseball cap and calls herself Mack, a fictional cousin of Mackie who's visiting town.
In the 1950 British thriller The Clouded Yellow, Jean Simmons cuts her hair and exchanges her dress for trousers in order to pass as "Master Fox". The disguise is never seriously tested, which is just as well as she's a remarkably unconvincing boy.
In Color of Night, Richie turns out to actually be Rose in disguise.
Connie and Carla, about two female performers who witness a murder, so they go into hiding by disguising themselves as Drag Queens (a spoof of Some Like It Hot where two jazz musicians who witness the St. Valentine's Day Massacre go into hiding by joining an all-women's jazz band). In other words, they dressed up as men who dress up as women.
Dragonslayer: Valerian dresses as a man to escape the lottery that sacrifices virgin girls. She eventually drops the disguise however, after Galen had already found out about it (the villagers mostly already knew).
In the 1979 basketball comedy Fast Break, D.C. (Harold Sylvester) admits to Coach Greene (Gabe Kaplan) that he has unusual feelings for his (ostensibly male) teammate Swish. In the climactic game, Swish unwraps her breasts and hits the court. D.C. is relieved.
In Frank And I, a young girl convincingly (in the movie) pretends to be a boy up until her master makes her drop her pants and beats her with a whip. When he scolds her for crying, she confesses that she's a girl and she loves him.
The heroine from the wuxia, The Golden Sword, would travel the land while disguising herself as a male beggar.
Harriet:
- Harriet dresses as a male sailor in one of her disguises.
- In the climax, one of the runaway slaves is biracial and can pass for her father's son. She dresses as a man, lowers her voice, and keeps her nerves while talking at a checkpoint. It fools the other men, though not Gideon who knows that the man in question has only daughters.
Head in the Clouds: Gilda sneaks out of Cambridge University dressed as a man so Guy won't get in trouble over her being in his room.
When the heroes are travelling to the prison camp by fishing boat in Hot Shots! Part Deux, Ramada disguises herself as a man since only men are allowed to fish. When they are stopped by a patrol boat, the disguise initially works, but then their cover is blown when Ramada, still in disguise, goes into the ladies restroom revealing the ruse.
There's a Soviet movie, called Hussar Ballad, whose protagonist, Shurochka Azarova, is the Trope Namer for this trope in the Russian counterpart of TV Tropes.
This trope is the central plot of Just One of the Guys, an 80's teen comedy. The main character's brother even asks sarcastically if she's trying to become a rabbi.
Juliana: Juliana asks her friend Clavito whether his boss, Don Pedro, would let her work for him. Clavito refuses and tells her that only men can work as ambulant singers. When Juliana's stepfather steps up with his abuse, she decides to run away from home and pretend to be a boy named Julián so Don Pedro would accept her. While her hair was already fairly short, she trims it so it becomes shoulder-length and stylizes it to look like a boy's hairdo. She also puts on a shirt and pants —at the time, women only wore skirts or dresses. It helps that, because of her young age, she's androgynous enough. It makes her unwilling to swim at the sea when she and the other kids go to the beach.
In Slapstick comedy The Knockout (1914), the hero's girl does this to watch him fight in a boxing match, since no women are allowed in the audience.
Fang Shao-Ching, the Action Girl of Legendary Weapons of China spends the bulk of her screentime dressed as a male. Justified by the film's setting in an Imperial Chinese Dynasty, where women aren't allowed to roam freely in public in the capital city. One of the other characters even said she "looks exactly like a man.", which is more of an Informed Attribute, because she... looks like a lady in men's clothes.
The Limehouse Golem: Lizzie often goes out dressed as a man to enjoy freedom that a Victorian woman lacks. She's used to this, having worked as a drag king while at the dance hall. She also commits some murders this way.
In the 1923 silent film Little Old New York, Marion Davies plays an Irish lass who disguises herself as her dead brother so that she can inherit the fortune that was left to him. She falls in love with the guy who was next in line to get the money after her brother.
In Lockout, Emilie ends up the only woman in the middle of a space prison riot so Snow must disguise her as a prisoner in the hopes that they can sneak past the others. He does this by rubbing coffee, motor oil and dirty toilet water in her hair. The other prisoners still take an interest in her for being a "pretty boy" inmate, forcing Snow and Emilie to fight their way through anyway.
Magadheera has a scene where Princess Devi poses as a man to sneak into training grounds to be with her lover, the warrior Kala Bhairava.
The banquet assasination from Martial Arts of Shaolin has the resistance heroine, Sima-Yan, disguised as one of warlord He-Sau's officers to get close to her target, though before she can act she's promptly interrupted by another assasination attempt on the same guy by Jet Li's character.
Ma Vie En Rose introduces such a character (a tomboy who goes by "Chris") right at the end, right after Ludovic's parents have given in to the Double Standard.
The stoning crowd in Monty Python's Life of Brian, which also doubles as Recursive Crossdressing.
The Disney Channel movie Motocrossed involved a girl posing as her brother to enter a motocross race, after he breaks his leg. What makes this one more ludicrous is that the siblings have the same name (Andy, short for both Andrea and Andrew).
There is a Soviet comedy called My Dearly Beloved Detective about two female detectives with the last names of Holmes and Watson. At one point during an investigation they dress up to sneak into a club of bachelor men. The head of the club gets wind of this and states that all the members will undergo "an embarrassing examination"... which consists of every member being forced to give a gentleman's word he's male. Holmes passes. Watson has some problems, but an admirer takes the blame for her.
The Swedish movie Mitt liv som hund (My Life as a Dog) is about a 12 year old boy sent to live with relatives in the countryside when his mother contracts tuberculosis. One of his new friends, who is also the top player on the local boys' football team, is actually a girl. Keeping up the charade becomes somewhat difficult when she hits puberty and things start to grow ...
The Canadian short No Bikini shows that bath and this trope do mix sometimes. Robin, a 7-yr girl, hates bikinis, but girls must wear a swimsuit for a swimming class. So she pretends to be a boy so she can attend just in swimming trunks.
There is the 2003 Afghani film, Osama, the first film to come out of Afghanistan after the overthrow of the Taliban. The film is about a 12-year old girl who disguises herself as a boy in order to earn an income for her family, who are left destitute and with no way of earning an income after the death of her father and uncle. Osama is an unusually realistic example of the trope.
Pirates of the Caribbean: Dead Man's Chest: Elizabeth Swann disguises herself as a man to sneak on board a ship. Since she changes on the ship itself, her dress is found by a few of the sailors, which leads to a mad rush to find the stowaway naked lady. Also, at the beginning of On Stranger Tides, Angelica disguises not just as any man, but as Jack himself and gets away with it until he visits her to reclaim his name. Even then, he believes she's a man until he recognizes her by her fighting technique.
The runaway Jack from Pitch Black.
In Pope Joan, Johanna of Ingelheim (Johanna Wokalek) passes as a man within the Church and rises to the top, becoming The Pope.
Princess of Thieves centers on Robin Hood's daughter, Gwyn, who dresses up as a man to follow her father.
Princess Leia briefly disguises herself as the bounty hunter Boushh in Return of the Jedi, though this barely counts since he's also an alien.
- And since, at least in the Old Republic, female soldiers weren't a rarity—there are female pilots in Episode I who attack the Trade Federation control ship, not even going into the Expanded Universe or female Jedi.
Red Cliff: In the second movie, Sun Shangxiang (Zhao Wei) infiltrates Cao Cao's tent while disguised as a male soldier. She even befriends a burly member of the enemy troops in the process, and in the final battle she managed to stop said soldier from killing her by putting on a random helmet.
- Could be an Actor Allusion, Zhao Wei was also the titular character of Mulan: Rise of a Warrior.
In Robin Hood (1991), Maid Marian (Uma Thurman) attempts to escape an Arranged Marriage to the evil Sir Miles Folcanet by disguising herself as a boy and joining Robin's merry men. When the Sheriff of Nottingham attempts to lure Robin into a trap by having his lover impersonate Marian, Marian is forced to reveal herself to Robin to save him. She was more successful at impersonating a man examples, partly because Uma's fairly tall.
In another Robin Hood example, Maid Marian first appears dressed in armor and assumed to be male in Robin Hood: Prince of Thieves.
In Salt, Evelyn Salt disguises herself as a man in order to get into the White House towards the end of the film. Angelina Jolie makes an eerily convincing man.
The German film Schwarzer Jäger Johanna (1934), in which Marianne Hoppe plays a woman who joins the Black Brunswickers during the Napoleonic Wars to follow her loved one.
Viola in Shakespeare in Love, Shakespeare's Love Interest, who wants to be an actor. Hilarity and awkward situations ensue.
In She's the Man (a modern-day retelling of William Shakespeare's Twelfth Night, mentioned below), the main character disguised herself as a boy so that she could play soccer after the girl's team was canceled.
In 1952 swashbuckler Sons of the Musketeers (aka At Sword's Point) one of the sons is quite obviously a daughter (played by Maureen O'Hara), but absolutely nobody notices until after she takes her hat off.
In The Story of Robin Hood and His Merrie Men, Marian sneaks out of Prince John's castle and journeys to Nottingham disguised as a pageboy. The loose tabard actually does a pretty good job of concealing Joan Rice's curves.
In Sumo Do Sumo Dont (シコふんじゃった。, Shiko funjatta), a 1992 Japanese film directed by Masayuki Suo, a heavyset female manager volunteers to join the desperate sumo club to prevent disqualification after one of their members (and the boy she's in love with) breaks his arm during the third match of the league they'd fought desperately to compete in. On the day of the next match, she binds her chest with bandages and tape to pass as male... and loses terribly, as she's not a trained wrestler. During her match, she's violently throne from the ring and the bindings covering her chest are partially ruined which leads to one of her teammates calling our her name (Masakou) and briefly shocking the crowd after running to cover her exposed chest before anyone can see. The rest of the Sumo Club comes to her rescue by instead calling out a male name (Masou) and running to her aid before the judges can realize what's happened. The club members are so touched and inspired by her attempt that they manage to win the rest of the league matches.
Surrounded: Mo is a young black woman who's dressed as a man and presented this way to others. Tommy Walsh sees through it, while most people simply think she's younger because of her soft voice and slim build. Will Clay also sees through it later, calling Mo "Gal" immediately when they meet.
After her rescue from Fogg's Asylum by Anthony in Sweeney Todd: The Demon Barber of Fleet Street, Johanna dresses up like a boy in order to hide from Judge Turpin. Unfortunately, she almost gets killed by her own father, Sweeney Todd, when he fails to recognize her and takes her for a witness to his final vengeance upon the Judge.
The Disney live-action version of Swiss Family Robinson has Roberta (or "Bertie") do this, as she and her grandfather have been captured by pirates. Not very convincing, and The Reveal shows that she's a girl when her head wrap is pulled off to reveal... really short hair, but a suddenly more girlish face.
Katharine Hepburn takes her turn in Sylvia Scarlett.
French film Tomboy has a 10 year old girl move to a new neighborhood. Throughout the film, she passes herself off as a boy, even playing soccer without a shirt, kissing another girl, and swimming without a top. Before doing the last, she even fashions a thing to put in her shorts that mimics a penis bulge. However, given these very intense measures there's some debate about whether Laure's transgender.
In the 1984 Finnish comedy Uuno Turhapuro In The Army, the protagonist's wife takes her husband's place in the Finnish army for a short while against her will, with an extremely unconvincing haircut and stubble. What really gets her, though, is that no-one noticed a thing...not even while they were bathing.
A similar idea is used in Victor/Victoria, merely as a way to break into show business. Victoria's singing is apparently far more appreciated by audiences who think she's a gay female impersonator named Victor. The film makes a point that this takes some doing: Victoria is naturally a coloratura soprano (being played by Julie Andrews) but has to perform as a contralto so that her voice is deep enough to keep up the illusion.
Norma: YOU NO GOOD TWO-TIMING SON OF A BITCH! HE'S A WOMAN!
The Viking (1928): To join Leif's voyage of exploration, Helga dresses up as a Viking to board Leif's ship with the others. She does not bother to keep up her disguise for long, as Leif cannot turn back because of his falling out with Erik anyway.
Yellowbeard: Spoofed; one of the ship's officers is named "Mr. Prostitute" and is an obvious woman with a fake mustache.
Yentl followed this trope. The main character became a man in order to attend a school in Jewish Talmudic Law, which was forbidden for women at the time. It made for some really weird love triangles. ^note
In Young Einstein, Marie Curie dresses as Einstein's father in order to gain access to him in the asylum.

Literature

All the Murmuring Bones by A. G. Slatter has a female protagonist who disguises herself as a man to flee an arranged marriage. It helps that she's very tall.
All Men of Genius is about a woman who wants to attend a prestigious scientific academy which only accepts men, and who impersonates her brother to get there.
Despite female samurai and daimyo being not just allowed but commonplace in The Ambition of Oda Nobuna, Asai Nagamasa pretends to be a man for unclear reasons. Her "wife" is actually a boy, as well. Neither of them knew this when the (political) marriage was arranged.
In The Anubis Gates by Tim Powers, Jacky (short for her middle name, Jacqueline. Her real first name is Elizabeth) does this in order to infiltrate London's criminal underworld and track down the unnatural creature that killed her fiancee.
A thirteenth century French Arthurian Romance is arguably one of the earliest texts to use this trope. A woman, Eufeme ("Alas, woman!") gives birth to a daughter, Eufemie ("Alas, girl"; or, "euphemism", a way of speaking around the subject). Her parents decide to raise her as a son, named Silence ("Seriously, could the metaphor be more clear?"), so that she can inherit her father's land. She becomes famed as a minstrel and a knight, captures Merlin, and is unmasked. Unfortunately, it's not quite as feminist as it sounds; Silence is depicted as the "perfect woman" precisely because she was raised as a man, and thus is not as susceptible to evil as other women are.
- Since Silence prefers being a man, albeit because of the social advantage it affords him/her, s/he could be considered a trans man by today's standards.
In The Artushof Berklinger tries to avoid his daughter getting married by dressing her up as his son instead.
John Carter of Mars: Tavia from the Barsoom-novel A Fighting Man of Mars; she dresses like a man to escape slavery and the harem of Tul Axtar. She can also fight much better than most women in the Barsoom-series.
The Beatryce Prophecy: In a land where it is illegal to teach girls to read or write, a mysterious young girl, wracked with fever, is found at the monastery of the Order of the Chronicles of Sorrowing. All she remembers about herself is her name: Beatryce. To protect Beatryce, who can read and write, Brother Edik cuts off her hair, disguises her as a boy, and lets her stay at the monastery.
In Becky by Lenore Hart, Becky Thatcher (Tom Sawyer's childhood sweetheart) passes herself off as a man and fights in the Civil War.
Robert Louis Stevenson's The Black Arrow: Sir Daniel's soldiers force Joanna Sedley to wear male clothes when they whisk her away from her guardian so nobody recognizes their kidnap victim. Joanna exploits her unwanted garment by pretending to be a boy named "John Matcham" to sneak out of the inn where she has been dragged to, borrow a horse and ride off without the landlord thinking of stopping her.
The Blair Witch Files - a novel spin-off of The Blair Witch Project - features this in its first book The Witch's Daughter. The backstory revolves around a young girl in the 1940s called Louise Irwin; after her parents and uncle die, her cruel aunt decides to send her to an orphanage. The boys' one is closer than the girls', so she forces Louise to pass as a boy called Lee. She's able to fool them for a whole year before the other boys notice that 'Lee' only ever uses the upstairs bathroom (with a lock on it), and out her as a girl. She no longer has to pass once she's taken to a girls' home, but she keeps calling herself Lee for the sake of her revenge plot.
Bloody Jack is a young adult novel about a London orphan girl who joins the Royal Navy as a ship's boy. Risky, but much more attractive than dying of starvation. This causes problems both comedic and poignant when she falls in love with a fellow ship's boy, thinks she's dying when she gets her period and has nobody to ask about it, etc. It has several sequels, and the character sometimes reverts to this trope in a pinch, even though by then she's filled out a little more and presumably no longer looks like an androgynous eleven-year-old. People still buy it, though.
In The Breadwinner, a girl named Parvana, who lives in Afghanistan, disguises herself as a boy in order to earn money for her family because her father was arrested and her brother was too young to provide for them.
Lydia of Brotherband dresses as a man to infiltrate the sex-segregated Arridan gold market along with Gilan in Slaves of Socorro. It helps that she's already fairly tall and muscular, and the flowing robes and kheffiyeh headdress she's wearing cover pretty much everything else. She's found out when her kheffiyeh is knocked off by a passing merchant, but by that point she's already set the place on fire.
The Brotherhood of the Conch: In The Mirror of Fire and Dreaming, Nisha disguises herself as a boy so she can attend the ceremony where Kasim and Ifrit are planning to overthrow the nawab.
In One Corpse Too Many, the second Brother Cadfael mystery by Ellis Peters, Godith Adeny (daughter of Fulk Adeny, foe of King Stephen of England) does this by dressing like a novice monk to prevent capture by the king, which would have caused her to be held for ransom. Cadfael deduces who she is quite quickly in the book. In the TV show of the book, he sees through her disguise instantly. As does the audience.
- In a later novel, done again by "Brother" Fidelis, and this time the ruse is successful. Even Cadfael is completely fooled until almost the very end of the eleventh book, An Excellent Mystery.
In the final book of The Chronicles of Prydain, Princess Eilonwy dresses as a man so she can go off to war with Taran and the others. Something of a subversion, since she fools absolutely nobody who knows her, but they sort of roll their eyes and put up with it because there's really nothing else they can do at this point. Besides, if she'd stayed behind like she was told, she would have been killed when Caer Dathyl was sacked.
City of Bones (1995): Elen, one of the few women to join the Magic Knight order of Warders, initially disguises herself as a man when she hires Khat to guide her through the Waste. He sees through it on the first day.
The Conqueror from a Dying Kingdom: A noble girl who's family members traditionally become scholars, dresses as a boy to become a knight. She did it, not because girls are forbidden from being knights, they are allowed even if it's uncommon, but to avoid the attention of her own family, which would have forbidden it. Even when not purposely dressing as a boy, she is androgynous, slim, and petite. Her disguise as a boy is paper thin and almost everyone at the Knight Academy sees through it, except for one person. She enjoys the way he treats her as One of the Boys so she continues the charade.
In Cue for Treason, the young runaway Kit, who joins an Elizabethan theatre troupe and proves good at playing female parts, is actually called Katherine.
Played with in Swedish author Ulf Stark's Dårfinkar och dönickar, in that the crossdressing is initially a mistake - Simone is assumed to be a boy called Simon. She becomes increasingly invested in her disguise as the story progresses, though.
Marion Zimmer Bradley's wizard Lythande is a woman who disguised herself to be able to learn magic; by the time her teachers found her out, she had learned too much for them to send her away. Instead, her punishment was that if any man should learn she was a woman, she would lose her powers, thus condemning her to continue the masquerade for the rest of her life.
- In her Darkover novel Hawkmistress Romilly runs away from home and disguises herself as a boy. She proceeds to fall in love with a man who seems to return her interest. Unfortunately it comes out that he genuinely prefers boys and is enormously taken aback, not to mention turned off, when he discovers she's a girl.
"Don't cry, mistress, I swear I won't touch you!"
(Romilly cries harder)
Twice for Eliza Sommers in Isabel Allende's Daughter of Fortune. First, Tao Chi'en has Eliza dress in a spare set of his clothes and tells people she is his brother, and mute on top of it. The next time, Eliza decides to go off on her own to look for Joaquin, the lover who left her for the Gold Rush. Dressed in men's clothes, she passes herself off as "Elias Andieta", a young man searching for "his" brother Joaquin. Her disguise works.
One of the tales in Boccaccio's Decameron features a daughter of the King of England traveling to Italy disguised as an abbot. She falls in love with a young fellow she meets on the way, but he is quite disturbed by her advances until she places his hand on her chest.
Terry Pratchett's Discworld
- Monstrous Regiment spoofs the everloving hell out of this one. Our heroine Polly Perks joins the army of her war-torn home country of Borogravia, under the alias of "Oliver Perks", to look for her strong-but-simple brother Paul. Along the way, she discovers everyone in her squad except the limp-wristed commanding officer, including the boisterous and apparently quite male Sergeant Jackrum, is also a woman disguised as a man, as are quite a few members of the Borogravian top brass. Pratchett also plays this for drama as much as for laughs, with Polly becoming disgusted by the contrast between how men and women are treated in Borogravia. What's really ironic is that when the regiment has to dress as women in order to infiltrate an enemy base, the male lieutenant is simply waved through, but Polly is assumed to be a man dressed as a woman and questioned. Even more ironic is when Jackrum states how so many of the upper brass are women and is then astounded to realize that every single one of them thought she was the only one in the army doing this. Oh, and the song exists in the setting. She took the name as a reference, but finds the joke gets old when people keep asking if she's heard of it.
- The performing troupe of female impersonators in The Last Continent included an actual female, who was filling in for her brother. And turned sideways because Rincewind honestly doesn't notice, though he did get upset that his (presumably male... ish) Luggage was now dressed in high heels (a lot of them) and a frilly pink tablecloth.
- An obscure Pratchett use of this trope, from the Assassins' Guild Discworld Diary, reveals that a few Polly Olivers had enrolled in the then all-male Guild school, by means of a short haircut and a note excusing them from gym classes. One former SPO became head tutor for Black Widow House after the Guild school went co-ed, and now teaches Edged Weaponry and Fencing.
Doctor Who Expanded Universe:
- Bernice Summerfield does it twice:
  - In All-Consuming Fire by Andy Lane, she disguises herself as a man while undercover in 19th century India. Once the Doctor finally notices, she explains she abandoned her original cover (as a woman looking for a husband) after she decked a man in a pub, and decided she'd draw less attention this way.
  - In the William Shakespeare pastiche "The Trials of Tara" by Paul Cornell in Decalog 2: Lost Property, she's disguised as Bertrand, and inadvertantly becomes one of Queen Strella's suitors. Strella doesn't realise, but her servant Miranda does:
    Strella: What say you, maid?
    Miranda: Yes, I say a maid.
    Have you been out of marriage too long?
Later, the Doctor arranges for the three suitors to join a troupe of female actresses as part of the Engagement Challenge, letting Benny engage in some Recursive Crossdressing. The spectators conclude that Bertrand makes "a twee and awkward girl".
- Deconstructed in the Doctor Who Missing Adventures novel The Plotters, where the Doctor's insistence on dressing Vicki up as a boy leads to her being sexually predated upon by a king with a fetish for young boys.
- The Missing Adventures novel The Ghosts of N-Space did a similar thing - Sarah Jane dresses as a boy for her own safety in the Middle Ages, and is repeatedly assumed by the other characters to be the Doctor's "catamite", much to her upset.
Don Quixote plays this trope perfectly straight with Dorotea, a girl who dress as a man who sets to get back her unfaithful lover in the first part of the novel. At the second part, this trope will be parodied and deconstructed
- The daughter of Don Pedro de la Llana parodies this trope showing us will use it in Real Life: The Ingenue who has been in a Gilded Cage all his life and asked his brother to show her the world... that is, the little town they live... at night. She dresses as a man because she wants to hide her identity. But nobody knows her because she had been hidden all her life. Justified because she is Just a Kid who has lived in a Gilded Cage and she really doesn't know better. As Sancho said:
  "In truth, young lady and gentleman, this has been a very childish affair, and to explain your folly and rashness there was no necessity for all this delay and all these tears and sighs; for if you had said we are so-and-so, and we escaped from our father's house in this way in order to ramble about, out of mere curiosity and with no other object, there would have been an end of the matter, and none of these little sobs and tears and all the rest of it."
- Clingy Jealous Girl Claudia Jeronima deconstructs this trope: She is wearing man's clothes because she has murdered a supposedly unfaithful lover and Barcelona is having a Civil War. She wants to conceal her identity so her family would not be harmed by revenge.
- The Exile Ana Felix deconstructs this trope: Fleeing for Spain for having a morisco father (former Muslim converts to Christianity), she enters Algiers, where the King blackmails her to steal his family treasure hidden in Spain. So she wears man's clothes to come back with the King's soldiers and mislead the Spanish authorities. She is captured by them and threatened with execution when she declares she is a woman:
  "A woman and a Christian, in such a dress and in such circumstances! It is more marvelous than credible," said the viceroy.
In the Ursula K. Le Guin short story "Dragonfly", in the Earthsea setting, Irian dresses as a boy in order to accompany the sorcerer Ivory to Roke, the wizard's school only boys are allowed to attend. Ivory's got his own agenda and Irian is actually a dragon born in a human body or something, in any case not really a girl, though she doesn't realize that until the end of the story.
Dragonvarld: Bellona dresses as a man when she's with Melisande in Idylswylde, since there a woman without a husband would be suspect (presumably while pregnant in particular). When warrior women from Seth come for them, they do this as a disguise too. Later while raising Ven, Bellona dresses and passes as a man for years, with other people believing she's his father.
The Elemental Trilogy: Due to entering Eton College, an all-boys school, Iolanthe is forced to disguise herself as a boy, going by the name Archer Fairfax.
Encyclopedia Brown Shows the Way: "The Case of the Girl Shortstop" involves a girl who'd been playing on a boys' Little League baseball team until one of her teammates ratted her out and got her kicked off, and she seeks Encyclopedia's help in finding out which one—Then ends up thrashing the boy for it in the solution.
In the third Finnegan Zwake novel, Uncle Stoppard's novel uses this with Ophelia/"Osric". Seriously.
In Walter Scott's ballad The Fire-King, Rosalie goes to fight in the Crusades dressed as a page. Her main purpose, though, is finding and ransoming her beloved Albert who has been taken prisoner. However, Albert in the meanwhile has fallen in love with the Sultan's daughter and changed sides, and he ends up unwittingly killing Rosalie on the battlefield when she throws herself in his way to shield King Baldwin. Apparently, at least because of her heroic death nobody at all comments on the fact that she was dressed as a man, and she is buried with honours "in Salem's blessed bound".
Florinda: Florinda dresses as a man to escape her father's incestuous intentions for her so she can pass for male, and no one's the wiser at first.
In The Folk Keeper, Corinna disguised herself as a boy named Corin to become a Keeper, since girls aren't usually allowed to take the position.
In From a High Tower, Giselle Schnittel temporarily pretends to be a man named Gunther von Weber in order to enter sharpshooting contests and win money to provide for herself.
Inverted Trope in The Galaxy Game by Karen Lord: Conventional wisdom has it that only a woman can be a corporate nexus (the power brokers of Punartam's highly complex social economy), so one character who was born a boy but had a clear talent for it was raised female. From what she says, it's possible she's had surgery, but she doesn't appear to identify as female, exactly, so much as identify so strongly as a nexus that she'll be whatever gender makes that happen.
Michelle, the main character in Elaine Moore's Get That Girl Out of the Boys' Locker Room, becomes this trope so she can play on her school's boys' football team.
Show Within a Show example: In Gilded Latten Bones, one of Jon Salvation's comic plays used this trope, starring a princess who was raised as a boy and crowned king by her unsuspecting subjects. Apparently this trope hit it off big in TunFaire, as lots of other playwrights immediately stole the idea and wrote their own variations.
In The Girl Son, Imduk, a Korean girl, is disguised as a boy so that she can attend school, at a time when it was believed only boys could learn the Chinese language, with the approval and knowledge of the school's principal.
In The Goblin Emperor, Maia has an aunt who disguised as man and became a pirate captain. She is also married to a woman. There is also an aversion, with Kiru Athmaza whom her boss tried to pass off as male to fill a prestigious position at court as no suitable male candidates were available. Maia sees through it immediately, and it is lampshaded both with her saying "I told you he'd notice" and Maia noting her voice is much too high to be mistaken for male. Maia being Maia, he gives her the job anyway. It is possible the disguise failed partly because she was ^not^ crossdressing; the uniform she wears for her job is implied to be the same for women and men.
In Grent's Fall, Ava Carleton disguised herself as a man to actively assist Henry Darro's rebellion, at least when others were around.
The Harry Turtledove alternate history novel The Guns of the South features Molly Bean, a prostitute who disguises her flat-chested self as a man to serve in the Confederate States' unit Castalia Invincibles. She poses as her "cousin" Melvin Bean and joined because the war was taking away all her customers. Ignorant and illiterate, she learns to read and begins to fall for her teacher. How much combat did she see? She was at Gettysburg, y'all. She later serves a surprisingly vital role in defeating the AWB men who are time travelers, by being a popular bedmate while covertly spying on them. Her letters to her lover describe many futuristic marvels (None of which she understands, but her teacher/future husband twigs onto the fact that these guys are from the future). These prompt him to instruct her to go to Confederate President Robert E. Lee and describe everything she'd seen. She does, but her attempts to hide her womanly self make it difficult (Lee can't figure out why she keeps on mixing up "I" and somebody named Melvin in her story). When the CSA goes after AWB, she shows back up in uniform and the commander's reaction ("you still haven't grown a beard?") makes it clear he knew all along about Molly but decided to keep it quiet due to her courage. After she helps take down the AWB, she marries her teacher. In Real Life, there was an actual Molly Bean who enlisted in the Invincibles, but she was discovered and sent home - in February, 1865, more than 2 years after joining the unit. Her livelihood as a prostitute was pure author's invention.
In Edward Eager's Half Magic a young girl gets really annoyed at Lancelot so she wishes that she was his match in strength and skill, then conjures a suit of armor and challenges him to a duel. She wins and the crowd cheers her. When the king asks her to remove her helmet she does so, having forgotten she still looks the same underneath. As the mood of the crowd shifts from shock to anger, she's called names and Lancelot is jeered for being beaten by a girl, for all of five minutes before Merlin erases everyone's memories.
Lampshaded with Blabbermouth in Haroun and the Sea of Stories by Salman Rushdie. "Don't you know girls have to fool people every day of their lives if they want to get anywhere?" When her secret is revealed, the only character bothered by it is quickly chagrined by someone more awesome who isn't.
When Matty joins Robin and the gang on their outlaw raids in Hawksmaid, she disguises herself as a teenage boy.
In Stephanie Kennedy's 1980s YA novel Hey Didi Darling this trope is the main plotline. A Girl Group decides to dress up like boys and form Tommy & The Tigers in order to get gigs.
Georgette Heyer has several examples:
- In These Old Shades the street urchin "Leon" whom the Duke of Avon buys to be his page turns out to be "Leonie" halfway through the book, though it turns out Avon knew it all along. He's like that.
- In The Corinthian, heroine Penelope ("Pen") Creed disguises herself as a boy to run away from home and seek out her childhood sweetheart. Hero Sir Richard Wyndham penetrates the disguise almost immediately, but goes along with it when he accompanies Pen. He advises her to tell people she's named Penn "after the Great Quaker."
- The Masqueraders has an outstanding example in that not only is heroine Prudence disguised as "Peter Merriot", but her brother Robin poses as "Kate Merriot". The book being set in 1746 or thereabouts makes this a bit more believable than it would be in the Regency period.
Hoshi and the Red City Circuit: Late in the book Hoshi is disguised as a fisherman, using nanomachines to masculinize her face and deepen her voice and bulky clothes to hide her curves.
In Andre Norton's Ice Crown, Roane briefly and accidentally does this; her short hair and coverall convince the princess she's male, and when the princess gets a good look at her, she's astounded.
Charles/Charlotte Dunois of Infinite Stratos disguises herself as a boy while attending the school, with the purpose of stealing data from Ichika and his IS unit. Unfortunately, she got found out (and in the most awkward way possible) before she could succeed.
Nastily subverted in Iron Dawn, in the backstory of Barra the Pict: seeking her fortune in the male-dominated Mediterranean, she dresses up as a young man and joins a group of bandits. She need not have bothered, as the thugs were disappointed to discover that she wasn't a boy when they turned upon and gang-raped her.
Jaine Austen Mysteries:
- Pam disguises herself as a male building inspector to tamper with the guacamole in The PMS Murder.
- Also the case with Fiona Williams from Death of a Trophy Wife, who dresses in men's clothing during her meeting with Lupe where she intends to kill her.
Spoofed in Kat, Incorrigible; Kat disguises as boy and wants to run away to London. She gets as far as the front door of her house.
Rune, from The Lark and the Wren, passes as a boy to join the Bardic Guild, which only accepts men. Somewhat subverted in that she's fairly open about her gender with most people not directly connected to the Guild. Also, when she gets the apprenticeship and reveals her true gender, she is savagely beaten and both her instruments are broken. Considering they were planning to castrate "him" to keep "his" pure voice, this may have been a better fate. It turns out well enough in the end: She throws in with a group of freelance bards who lack the Guild's prejudices.
Deryn/Dylan in Scott Westerfeld's novel Leviathan disguises herself as a boy to join the air forces.
Alanna of Trebond from the Lioness Quartet books by Tamora Pierce. As a nine-year old she starts dressing as a boy in order to train for knighthood as Alan, and keeps it a secret until after she's already earned her shield (and thus is formally Sir Alanna).
- In one of the short stories set in the same universe, a character is revealed to have disguised herself as a boy and ran away from home because her stepfather wanted her to be veiled like the other females in their country and was going to arrange a marriage for her.
In the children's picture book Little Kay a girl dresses up as a boy to become a knight. The king somehow finds out there's a girl among the men, and asks his advisers how he can figure out which one she is. In an inversion of the Achilles myth, the advisers suggest offering jewels and pretty fabrics and so on, on the assumption that the girl will be the one interested. Since this is a comedy, though, the men all turn out to be raging dandies who love the gaudy stuff while the girl spurns it. The only one who offers useful advice is the castle maid, who suggests the king have them all drink a toast, since when they all tilt their heads back to drink the men's Adam's apples will be apparent. This proves effective.
After the girl is discovered, the sultan is so impressed that he decides to make her a knight anyway, since she is the only one in the army who isn't a complete dandy. Dressed as a boy, she goes off on a quest which will win her the hand of a princess. She rescues the princess, and the princess discovers she is a girl, but they decide to get married anyway.
- Possibly based on a Russian fairy tale - at the end of that story, the king asks the girl to bathe with him, she goes to change... and runs off, leaving a note behind saying "by the way, yes, I AM a girl."
  - There is an Italian tale which has the same scene (except the girl fakes an urgent message forcing her to return home). It seems to have inspired an entire film series
- There was a similar fairy tale, only that the whole group was a bunch of girls. When they got wind of the 'tests' to expose them, they would try to confuse things even more. When offered jewels and fabrics, some of them ignored them, some of them appraised the valuables, and a couple of them 'stole' some of the gems. When ashes were strewn across the threshold (on the assumption that the girls would try to clean it up), most of them marched right across it, while a few of them tried to clean it up and made the mess worse in the process.
Dernhelm/(Éowyn) from The Lord of the Rings is a classic example. She is able to kill the Lord of the Nazgûl precisely BECAUSE she is not a man.
- The Witch-King's belief that no man could kill him came from a prophecy by Glorfindel a thousand years before. The prophecy said "not by the hand of man shall he fall" and the Witch-King thought he was, therefore, invulnerable. But, he got shivved by a hobbit (not a Man) and his head struck off by a woman (not a man) working in tandem with each other (not singular), an old artefact made specifically to hurt him from back in the day (a weapon made by craftsmen) and a whole army supporting them to set his death in motion (in short, a team effort by loads of men, women and horses). Which just goes to show: you should always read the fine print.
Kim from Mairelon the Magician hides herself as a boy; she's a street kid, and, being a girl, would be put in a brothel pretty quickly if she was revealed.
The Majyk by Accident books Majyk by Hook or Crook and Majyk by Design feature a Welfie swashbuckler who prefers to be called "A Blade for Justice". Blade turns out to be Kendar's wife, Mysti who, whilst hiding a legendary bust and still wearing twinkly stuff on her eyelids, dies in a fight against a dragon because of a combination of the dragon's magical resistance and a poorly timed Disney-esque sword-throwing incident and is brought back to life by a rather stupid prince whom she had no intention of marrying. Both Kendar and Mysti took the "Til death do us part" deal pretty seriously. Hilarity ensues in Majyk by Design when they hook back up with Mysti still in costume and Kendar's brother and aunts in eavesdropping distance.
Miranda, the title character from Maledicte, passes herself off as a young man to get revenge on her lover's father. The male name and pronoun are used even in scenes from "his" point of view, which definitely makes for some odd sex scenes. Actually, the entire book is an odd experience - Maledicte's deception is so complete that the reader forgets that it is a deception.
Mayo Chiki!'s premise, or part of it, is that the female Subaru Konoe is forced to dress as a male butler.
In "The Misadventures of Maude March", the title character and her sister Sallie disguise themselves as men while Maude is on the run from several crimes, including murdering a man(which was actually her sister by accident). All the women, and the occasional man with a sister who did that, see through it, though most men are completely fooled.
- In the sequel, "Maude March on the Run!" they are forced to do this again when Maude is recognized and Sallie has to break her out of prison. Again, the trick only works on most men, because women apparently have a sixth sense for this thing.
The Mémoires du général Thiébault mention a girl known as M. de Marbitzky, a German nobleman's natural daughter who dressed as a man (and is referred to with male pronouns in Thiébault's narration). Unfortunately, there are no details about him and the reasons why he lived as a man.
Princess Miriamele in Tad Williams's Memory, Sorrow, and Thorn dresses as a servant boy when she wants to roam the Hayholt unrecognized, making this a cross with King Incognito. Her disguise is effective enough that the hero, Simon, is fooled (granted that he's not all that observant when it comes to girls), even after they meet in the wilderness. Wiser characters do see through it, though.
In Poul Anderson's A Midsummer Tempest, Jennifer dresses as a boy to escape her captors.
Judith, the teenaged protagonist of the young adult novel The Minstrels Tale, is forced into an Arranged Marriage by her stepfather. Not only is she deeply put off by her bridegroom, who is at least thirty years her senior, but on the night of their betrothal dinner she falls in love with the young minstrel who comes to play and sing for them. He leaves her an instrument and a note suggesting another way of life, which she accepts gladly; she cuts off her long hair, dresses in clothes belonging to her deceased brother, and runs away to minstrel school.
Eponine in Les Misérables for a while - she trades outfits (with a boy who is actually described as enjoying crossdressing for a lark) to disguise herself so she can sneak into the barricades. Marius doesn't even recognize her when she takes a bullet that saves his life and ultimately ends hers, but that might just be him being a silly, tactless and clueless emo kid.
In Stephanie Burgis's A Most Improper Magick, Kat tries to run away as a boy to cause a scandal. She doesn't even make it out of the garden.
Rosario in The Monk, who quickly soon reveals himself to be a woman named Matilda.
In The Mother Daughter Book Club, one character wears a boy's uniform and helmet to try out for the school hockey team, since the coach refuses to let a girl join. Naturally, her skills secure her a slot on the team, even after her identity is revealed.
Brady in Mr Blank and the sequel dresses as a man to facilitate her multiple allegiances in various conspiracies.
Alice in Beth Hilgartner's A Murder For Her Majesty takes this up almost by accident. Having witnessed her father's murder, apparently at the Queen's command, she needs to find a place to hide; conveniently she has a run-in with some helpful boys in the cathedral choir, who think it would be great fun to disguise her as a choirboy.
In My Father Had A Daughter, a fictionalized account of the life of Judith Shakespeare, the heroine dresses as a man in order to sneak off to the Globe Theater and act in her father's plays. Works well until he figures out who she really is, but even he has to admit some amusement at the trick. The narrative implies that her ruse was his inspiration for Twelfth Night (see the Theater section below).
Ikusu Mizutani from NAKAIMO - My Little Sister is Among Them! hides the fact that she's a woman while working for the Seiryuu Association. She does this not because she has to, but so as to keep up the illusion of her dream of being a ninja, as all ninjas were traditionally male.
Nick Velvet: In "The Theft of the Birthday Candles", Sandra Paris disguises her herself as a yoing man to take the place of the co-pilot on a flight she is planning to hijack. Her disguise is good enough that none of the men around notice, and it takes even Nick a while to figure who she is.
In A Night In A Moorish Harem, Persian beauty Myrzella recounts how she ended up in the titular harem. She was captured by Turkish bandits while on her way to her Arranged Marriage and was only able to escape by dressing herself as an boy and fleeing on a merchant's ship. However, Myrzella is handed by her master as an gift to an Moroccan pasha who figures out her gender and she ends up being forced into his harem.
Exactly the same thing happens in No Bed For Bacon, the novel upon which Shakespeare in Love was (very) loosely based.
Of Fire and Stars: Mare, a princess who likes to dress in a very masculine fashion, passes as a man when going into the city often and sneaking back into the palace at one point.
In John Barnes's One for the Morning Glory, Calliope dresses as a man. Characters pretend to be deceived. Sometimes even she forgets that she's dressed as a man and glares at people who refer to her as male.
In The Orphan Train Adventures book "A Family Apart", Frances (age 13) and her younger siblings are sent on the Orphan Train. Having promised her mother to stay with the youngest (a 7-year-old boy), and hearing that boys are more likely than girls to get adopted along with their siblings, she pretends to be a boy.
Another Robin McKinley example occurs in The Outlaws of Sherwood, when a young woman named Cecily joins Robin's band under the name Cecil. She remains undiscovered for quite a while, which is particularly impressive considering her brother Will is also in the band. And Marian disguises herself as a man for a shorter period in the same book.
Deconstructed in Patience and Sarah. 23 year old Sarah sets off to New York disguised as a man named Sam. However, her soft looks, high-pitched voice, and lack of facial hair means that she looks like 14 year old at oldest. She repeatedly gets in trouble when people try to arrest her for being a runaway apprentice.
Paths of Darkness: Le'Lorinel is actually a female elf, dressing up as a male. She mostly uses this disguise in order to deflect attention from the fact that she is in fact Ellifain, the young elf child that Drizzt rescued in The Dark Elf Trilogy.
This is the main storyline of the historical novel Pope Joan (based on what may have been a Real Life example as well, but is generally considered fictitious).
In The Price of the Stars, Beka Rosselin-Metadi is targeted by assassins and has to fake her death to throw them off. She then creates a cover identity for herself that is as different as possible from Beka Rosselin-Metadi in several respects, including presenting as male.
Queen of the Tearling has an unusual example; Kelsea swaps clothes with one of the male guards who accompany her. The loyal guards know that she is a woman, and the disguise is not meant to be very convincing, it is only to distract the enemies, who are looking for the Queen and are unlikely to get very close.
Ratburger: Discussed when Zoe wonders if Tina's secret is that she's really a boy named Bob.
The Raven Tower: Discussed; the nation of Iraden bars women from military service, so Tikaz mentions that some women assume male identities to become soldiers. When he's receiving medical treatment, Eolo clarifies that he's a transgender man, not this trope.
Bio of a Space Tyrant: Nearly every character in Refugee ends up dressing as a member of the opposite gender as a defense against ubiquitous space pirates. Ironically the captain of one pirate spaceship turns out to be also hiding her true gender; she takes the protagonist's kid sister (also in disguise) in as a cabin boy in exchange for both parties maintaining each other's secret.
The Reluctant King: Margalit disguises herself in a man's clothes when she goes to help Jorian on mount Aravia. The narration does mention that her disguise is kinda given away by some unmasculine bulges underneath her jerkin, though other strangers mind their own business.
Rose Daughter, a retelling of "Beauty and the Beast" by Robin McKinley, has Beauty's sister Lionheart disguise herself as a boy so she can get a job and help support her father and sisters. This somewhat confuses their new neighbors, who are quite sure that when the family moved in there were three daughters rather than two daughters and a son, but they shrug it off and go about their lives.
Sarum: Aelfgifu dons Saxon armor to fight a skirmish against the Vikings and is initially mistaken for a young man, as she'd intended. Subverted in that her deception never fools anyone for long, but she fights well enough that her brothers insist she be allowed to participate in the Battle of Edington without having to invoke this trope.
The Secret Of 1798: Catriona dresses up as a boy so she can go fishing with her father. She simply borrows a neighbour's clothes and hides her hair under a large hat. The ruse is up immediately when the boat capsizes and they are rescued by a French ship.
Seven Daughters And Seven Sons: Buran disguises herself as a boy in order to make her family rich, since her father has no business sense. Sweet on Polly Oliver ensues.
The Shadow Campaigns:
- Winter Ihernglass escaped from an Orphanage of Fear by enlisting in the Vordanai army. She's one of the only rankers in the First Colonials who volunteered for service in Khandar, as it was the furthest posting possible from Vordan and the least likely to contain anyone who'd recognize her. The reader is in on her identity from the first chapter, but not anyone else; frequent mention is made of the fact that she would be dishonorably discharged if her true sex became known. (She initially gets away with it by pretending to religious sentiments in order to avoid the other soldiers' brothel and tavern visits. Her Rank Up in the beginning of the first book also helps, as NCOs get private quarters; previously she had purchased her own tent out of pocket to avoid sharing quarters.) Lucky for her, when her CO eventually does find out, he decides to keep up the masquerade, as she's far too competent to let go.
- Bobby is revealed to be female about three-quarters of the way through The Thousand Names, when she suffers a grievous wound in combat. Her fellow noncoms also decide to keep the secret, although this has more to do with the nature of her survival than her sex. (Hint: she undergoes an Emergency Transformation that would see her executed for witchcraft back in Vordan.)
The Shakespeare Stealer: One of the "boys" in Shakespeare's company is revealed to actually be a girl who disguised herself as a boy so that she could become an actor, since it was illegal for women to perform on the Elizabethan stage. She managed successfully for a while, but was eventually revealed when she received an injury to her chest during swordfighting practice and the teacher insisted on opening her shirt to see the extent of the injury, only to find that her chest was suspiciously wrapped underneath.
Shield Of Three Lions has the main character, a young girl, dressing up as a boy to save herself from being killed off or married for her property. She ends up going off to the Crusades and falling in with King Richard. Among other things, he falls in love with her as a boy and there is much confusion and danger (since he's the king) when he realizes she's a girl.
Liveship Traders: In Ship of Magic, after Althea runs away from her family, she asks a friend for advice on how to find work as a sailor on her own merits; the friend snarkily responds that she would have to find a way to be reborn as a boy, preferably one with a different last name. Which is exactly what she does — she disguises herself as a boy, and joins a crew under an assumed name.
Signal Airship: The protagonist, Josette Dupre, used to be one of these before the Garnian military allowed women to serve in a (limited) military role.
Skugg-/Shadow: Caroline spends large parts of the books pretending to be a young man called Carl. She does it for several reasons: increased freedom, to gain a certain job, and for the sheer heck of it. She will also quite happily flirt with both men and women. (Which backfires when two of them fall deeply in love with her and decide to marry each other, bonding over their mutual love for Carl. Yeah.)
Someone Else's War: Ruth Mallory. She doesn't get the idea until someone else mentions it, however, and wishes she had thought of it much sooner.
A Song of Ice and Fire:
- Arya Stark has this trope forced upon her, although she was something of a tomboy in the first place. In the first book, her unkempt, tomboyish appearance leads to lots of people mistakenly calling her "boy", and she has to correct them so often that "I'm not a boy" practically becomes her catchphrase. In the second book, once she's in disguise and actually trying to pass off as a common boy, when someone sees her ruse she has to repeat her catchphrase with a twist: "I'm not a girl!"
- Brienne is an interesting case in that she does look like a tall, powerfully-built man; she would have a harder time trying to look feminine than to pass as a man. As she's one of the strongest knights in the Seven Kingdoms, she was able to secure a place in Renly's guard without actually needing to hide. The only way you could tell her actual gender is by seeing her bareheaded, which leads her to keep her helmet on when she'd rather not be recognized.
- While it hasn't been explicitly revealed as of yet, the half-Summer Islander, slim, smooth-faced Dornish Alleras with the widow's peak who's not interested in women bears a striking resemblance to the half-Summer Islander, slim, Dornish female Sarella whose father had a widow's peak.
- Deconstructed with Brave Danny Flint, the subject of a romantic song, who posed as a boy to join the Night's Watch. Apparently the real "Danny" Flint was raped and murdered, presumably by her fellow soldiers when her identity was discovered. Just another average day in Westeros.
Split Heirs: Ubri, a Gorgarian woman, dressed up as a man to seduce Arbol... unaware that the latter is herself (unknowingly) a disguised girl.
Star Wars: In one of the novels, Princess Leia debates trying to pass herself off as a man. She takes a good, long look in her mirror, and decides her figure is far too emphatically female. (Probably intended as an ironic reference to her Sweet Polly Oliver turn in Return of the Jedi)
The Stormlight Archive:
- Shallan successfully uses a boy's or a man's disguise several times in order to gather information or pass unnoticed through war camps. Nobody ever notices, but then she is a mistress of illusion.
- High Marshall Azure in Oathbringer pulls this. Considering how strongly enforced Vorin gender roles are it's even more scandalous there than it usually would be. It is, however, subverted in that all of the soldiers under he command know she's a woman, and she makes no effort to hide it from them, it's just that no one outside the army knows she's a woman.
Swiss Family Robinson: The old man's granddaughter is disguised as his grandson.
Sword of the Rightful King: Gawen turns out to be Gwenhwyvar, aka the future Queen Guinevere. Even the narrator is in on the trick, since the sections told from her point of view continue to use masculine pronouns.
Tales of the Fox: Van's daughter becomes a Sweet Polly Oliver — Van is horrified at her "unwomanly" desire to fight, while the normally tricky Fox is dismayed at how easily he was fooled by a false beard and deepened voice.
The Third Witch, a retelling of Macbeth, has the main character Gilly disguise herself as a serving boy to infiltrate Macbeth's castle. He killed her father to marry her mother, the future Lady Macbeth. Gilly has vowed to avenge her loss by killing Macbeth whenever she gets the opportunity.
The Tokaido Road: The main character Cat travels through feudal Japan dressed in several male disguises. It seems that a lone female traveler would be unusual but not impossible; the real reason for the cross-dressing is to evade a warrant for her arrest. In an interesting reversal of the Attractive Bent-Gender trope, Cat's love interest sees her as an attractive male monk and considers taking "him" to bed. Once the love interest discovers Cat's true identity, he's impressed and has no problem transferring his attraction onto the true female version.
Tokyo Ravens: Natsume is a boy as far as anyone outside of her family knows due to family tradition. The "tradition" was created so that the family's enemies would target her rather than the actual heir, Harutora.
Toliver's Secret: For her mission to deliver a message to the revolutionaries after her grandfather's too injured to do it, Ellen pretends to be a boy by wearing her older brother Ezra's hand-me-downs, having her hair cut short for a pigtail, and going by her surname, Toliver. Ellen's mother, Abby, originally suggests doing this herself, but Ellen's grandfather dismisses the notion because she'd fool "no one but an idiot". He believes Ellen is more convincing for the job because nobody would suspect a small boy with a loaf of bread (which the message is hidden inside).
To Shape a Dragon's Breath: This is what Karina Kuiper did to join the dragonthede—the military—at a time where only men were allowed to be part of it. She disguised herself as a man and was claimed by a kessseldrach dragnet. Six weeks into her military service she was found out as a woman and her case went to the High Moot, where the court decided to allow her to prove herself as skilled in battle as war maidens of folklore. She successfully did so, remained in the military, and now has a military pension.
The Tough Guide to Fantasyland: One Tour Companion, the Slender Youth, is very often a girl in disguise as a boy (she's usually a Princess).
Tunnel in the Sky features an example where "Jacqueline Marie Daudet" is mistaken for a young boy (in part due to constantly wearing body armor) by another boy during an advanced survival test on a far away planet. She continues to pretend that she's "Jack Daudet" for weeks, including through some sexist commentary by her survival partner, until the beans are spilled by someone the two of them rescue. For 1955, the premise that girls could do things just as well as men could was pretty advanced.
Undefeated Bahamut Chronicle: Aeril disguises herself as the male "Coral" in order to infiltrate the Seven Dragon Paladins. This isn't so she can be a Drag-Knight (in this setting, female Drag-Knights are not only common but make up the majority of skilled Drag-Knights) but because her real identity (a princess of an ancient civilisation) would attract too much attention. Unusually, her disguise involves no physical component beyond wearing male clothing; she uses her ability to control people's perceptions in order to pretend to be male.
Under A Painted Sky: Samantha and Annamae run away by posing as boys and taking the Oregon Trail west.
An Unkindness of Ghosts: Theo disguises Aster as a boy named Aston to sneak her into Lieutenant's coronation.
The Wide-Awake Princess: Annie starts her search like this. Once she joins Liam, she readopts a dress.
Will in Scarlet: Much is actually the miller's daughter, masquerading as a boy as a way of protecting herself.
The Witchlands: Merik initially thinks that Cam is a girl who masquerades as a boy so that she could enlist in the Navy. Turns out not to be the case, as Cam's a transgender boy.
In "Yentl the Yeshiva Bocher", a short story by Isaac Bashevis Singer, the book which Barbara Streisand's famous movie was based on, Yentl dresses up as a man so that she can study Talmud at yeshiva, an activity restricted to men at the time. She falls in love with a guy (Avigdor) who thinks she's male, while a girl (Hadass) whom the guy (Avigdor) is in love with falls in love with her (Yentl). One of a rare small number of circular love triangles. Unlike in the movie, Yentl does not get a happy ending. She is exiled from the town and spends the rest of her life wandering around dressed as a boy, trying to study wherever people haven't heard of her. That's what actually would have happened, seeing as in America women couldn't study Talmud either.
The Zucchini Warriors: The star of the Macdonald Hall football team is in fact Cathy Burton from the girls' school across the road, wearing the name of school nerd Elmer Drimsdale (who has to keep up the ruse out of uniform). The resulting fame goes to his head a little.

Live-Action TV

ABC Afterschool Special: In "A Different Twist" Christi pretends to be a boy because she wants to play the title role in Oliver! and the director refuses to let girls try out.
Ashes of Love:
- Jin Mi pretends to be a boy (with the help of a magic hairpin) when she first arrives in the Heavenly Realm, and later while hiding in the mortal realm.
- Kuang Lu dresses as a man when she enlists in the army.
Spoofed by the character of 'Bob' in the various Black Adder series.
- Queenie makes a very poor attempt at this (wearing a big cloak over her elaborate dress) in an attempt to join in on the boys' drinking party.
- Also used for a bit of subtle Character Development; in the second series (set in Elizabethan England), when 'Bob' first shows up, Lord Blackadder is both taken in by Bob's disguise and highly attracted to 'him', prompting something of a crisis of sexuality. In the fourth series (set during the First World War), 'Bob' shows up again... and Captain Blackadder's not fooled for a second. Unfortunately, his superior officer is...
- In the same episode, Baldrick attempts an inversion where he disguises himself as a woman to try and seduce the General to marry him for his wealth (yeah...). Blackadder scuttles the plan by pointing out that the General is unlikely to be attracted to a "two-legged badger wrapped in a curtain".
- In a later episode 'Bob' is going by 'Bobbie' (not her actual name of 'Kate'), wearing more gender-neutral clothes, and openly sleeping with Flashheart; it's not clear if she came clean and somehow kept her job or if the General is just that oblivious.
The Brittas Empire: Subverted in “Pregnant”. When a urine test reveals that Tim has apparently gotten pregnant, Brittas accuses him of disguising himself as a boy to get around the filled quota of women in the leisure centre, going so far as to try to remove Tim’s clothes. It turns out that a mixup had occurred and that the actual owner of the urine was Julie.
Carry On Laughing!: In "The Baron Outlook", French knight Sir Gaston de Lyon, about to be captured by the English, swaps clothes with his mistress Marie, who then pretends to be him. Sir Gaston does get a little excitable in the process, however.
A subversion comes in a Chicago Hope episode where at the start we see a teenage girl hack off her hair and attempt to pass as a boy on the streets. The subversion comes with The Reveal that the girl is actually a boy that was simply raised as a girl after a botched circumcision.
Cinderella Chef: Jia Yao dresses as a man because that always works as a disguise on television. Then she discovers no one is fooled by her disguise.
Cold Case had that 2-part Boot Camp Episode about a girl who joined a military school to prove she can hack it with the best of them. She only found later that her classmates didn't like it not because she was a girl but because she was a "barracks rat", an anti-social loner. Only when she softens do they warm to her. She gets killed by another jealous barracks rat
Brazilian miniseries Copas De Mel had a woman disguising as a man to travel with the Brazilian team for the 1958 FIFA World Cup. On renaming, she decides to use the same nickname as her actual, Mel - from Amelia to Melchiades.
In Daddy's Daughters, Eugenia (Darya Melnikova) disguises herself as a boy to help the school win a football match in Episode 35. It helps she was a Pettanko Bifauxnen early in the show's run.
Dickinson:
- Emily and Sue dress in men's clothing to attend a lecture at Amherst College.
- Emily later imagines herself as a Civil War soldier in uniform during battle, when women did not serve openly (though a large number cross-dressed during the conflict for this).
In William Hartnell-era Doctor Who, the Doctor would often dress up his female companions in men's clothes out of concern for their safety:
- In "The Crusade", the Doctor insists on dressing Vicki up as a boy because he feels this will make her safer in the Middle Ages. Vicki tries her best and the disguise works well, but eventually complains to the Doctor that she's fed up with being a boy and wants to be a girl again. She spends the rest of the story in a stunning and very feminine medieval gown and headdress, which she seems a lot more comfortable with.
- In the later Hartnell story "The Smugglers", Polly is dressed fashionably for the 1960s in trousers and a cap. When she goes back in time to pirate Cornwall, the locals mistake her for a boy, which she admits to the Doctor makes her feel 'very odd'. The Doctor tells her it's better she go along with it for her own safety, as pirates do not tend to be kind to women.
- In "The Woman Who Lived", Ashildr disguises herself as a highwayman. A flashback to the Hundred Years War also reveals that she Bound and Gagged a male soldier and stole his weapons and uniform in order to join the fight.
Played for laughs in an episode of Family Matters. Laura is buying her first car and sees one she likes, but the sexist salesman doesn't take her negotiations seriously. She disguises herself as a boy by borrowing Eddie's clothes (very baggy on her due to her brother's height), a baseball cap to hide her hair, and of course putting on a deep thuggish voice, and goes back to him to do business. The salesman isn't fooled and rips her hat off, at which point she becomes super-feminine and pretends to cry until he lowers the price.
Farscape did this in the episode "Coup By Clam," when Moya was orbiting a planet notorious for its torturously sexist laws. When a tech was sent over to help, everyone assumed he was male, but Chiana was never convinced and eventually forces a Gender Reveal. As Chiana herself put it "I know a male when I see one." Unfortunately, the tech's boss wasn't so understanding, and came within inches of killing her before Scorpius intervened.
The First Shop of Coffee Prince has this trope as its main plot.
The Friday the 13th: The Series episode "The Poison Pen" features protagonist Micki dressing as a male monk to infiltrate a monastery.
Game of Thrones: Arya Stark is disguised as a boy by Yoren to hide from everyone and be taken to the north to safety due to her status of being branded the daughter of a "traitor". After a while, Surprisingly Realistic Outcome occurs and it becomes a Subverted Trope: Arya is only able to conceal her gender from truly stupid people, while anyone with a working brain (Gendry, Tywin, Jaqen, The Hound) sees past the disguise at first glance. By the third season, she's more grown up and it's pretty obvious to people that she's a girl. Before her disguise, there's something of a minor Running Gag in her doing this unintentionally. She dons pants while practicing with her sword, and people who encounter her during these moments often mistake her for a boy, much to her frustration.
- In episode 1.4 of House of the Dragon Rhaenyra dresses up as a boy to sneak into the bowels of King's Landing with her uncle Daemon. To be exact, they go to the Street of Silk. She really doesn't look very masculine in her disguise, just poor. It does fool some people, but not all.
General and I: Bai Ping Ting disguises herself as a man to sneak into Jiao Yan Casino.
Goodbye My Princess: Xiao Feng and A Du are disguised as men when they meet Mi Luo.
Korean drama (and a Japanese remake) Hana-Kimi, with a girl pretending to be a boy to go to an all-boy's school to meet the high jumper she has always admired. Of course, as a twist, he figured out she was a girl by the first/second episode but purposely didn't tell her that he knew.
In Korean drama, Han Guk Young, Sujeolnyeo Seo-ssi (Lee Tae Ran) dresses like a man and goes out spying at night.
Hanna: In "The List," Hanna disguises herself as a young man to infiltrate the hotel.
In Help! I'm a Teenage Outlaw, Deedee spends a lot of time disguised as a boy. It helps that most people don't expect a teenage girl to be part of a gang of highwaymen.
Interview with the Vampire (2022): In the Season 1 finale, Antoinette Brown — who has been a vampire since at least the sixth episode — has disguised herself as a man in order to spy on Louis de Pointe du Lac and Claudia and read their thoughts, which is why she's aware of their plot to murder her lover Lestat de Lioncourt.
Irma Vep: Irma dresses up as a man to fulfill a criminal ploy, which results in Mira doing the same while she plays her.
Dee in the It's Always Sunny in Philadelphia episode "The Gang Gets Invincible". This being It's Always Sunny, and Dee being... Dee, as soon as she takes off her disguise, she breaks her foot while trying to kick a football.
The King's Woman: Gongsun Li dresses as a man after her grandfather's death. It's an unconvincing disguise to say the least.
Tom, Leo's fellow apprentice in Leonardo, is a girl who disguised herself as a boy to escape an arranged marriage and because in Renaissance Florence girls can only paint as a hobby. Her real name is Lisa, which given the series' In the Past, Everyone Will Be Famous tendencies, presumably makes her Lisa del Giocondo. (This is confirmed in Episode 8.)
Lost Love in Times:
- Qing Chen disguises herself as a male soldier to escape notice.
- Duo Xia pretends to be a man when she challenges Yuan Ling to a duel.
- Ming Yan dresses as a man while pretending to be Mo Bu Ping's student.
Mendol Ikemen: Three girls pose as male idols.
The 2000 mini-series Merlins Apprentice has newbie mage Jack attacked by knight Brian, who thinks he's a threat. A desperate Jack casts a spell to make Brian like him and is shocked when the knight starts kissing him. Before Jack protests he doesn't feel that way, Brian tears open "his" shirt to reveal wrappings around her chest and that she's really Brianna. To his credit, Jack can't take advantage to release her from the spell. Merlin stops Brianna from killing Jack, musing that her commanding officer "must be old indeed not to realize" his top knight is a woman.
- Likewise, when friends Yvonne and Graham see the pair kissing, they realize the truth about "Brian" and muse on how they couldn't see it before.
Miss Fisher's Murder Mysteries: The Victim of the Week in "Murder and the Maiden" is a nurse who has adopted the identity of an institutionalized RAAF officer in order to fly.
In the Darkest Africa sketch in episode 29 of Monty Python's Flying Circus, the explorer called Brian is obviously Carol Cleveland disguised as a man, though no special attention is drawn to it.
Murdoch Mysteries:
- In "Shipwreck" this turns out to be the Big Secret of a priest suspected of murder.
- A season 3 episode, "Victor Victorian" featured a whole group of women masquerading as men. Murdoch later notes that he should have realised that the Victim of the Week was actually female because 'he' owned more than two pairs of shoes.
My Country: The New Age: Hui-jae dresses as a man when she puts up posters around the city.
The Nanny: In "Stock Tip", Fran Fine disguises herself as a man to sneak into a men's only club where she has to stop Maxwell Sheffield from striking a deal with an alleged stockbroker. Hilariously, the establishing shot starts off with a waitress who looks like Fran offering a drink to a man, who turns to the camera to show the disguised Fran. When she finally reveals herself to Maxwell, Maxwell admits he was feeling strangely attracted to her disguised self.
Variation in Our Flag Means Death: It's a series about pirates, so of course the suspiciously mute pirate with an even more suspicious fake Gag Nose and beard is a woman in disguise. Their gender identity is revealed, but Jim is nonbinary rather than female.
Also the heroine in the Korean drama The Painter Of The Wind.
In the Chilean Soap Opera Pampa Ilusion, the female lead is a young and beautiful doctor who wants to get close to her misogynistic Jerkass of a father, who disinherited her and her Missing Mom when she was born. To do so without being found out, she crossdresses as a male physician, and unwittingly attracts men (like the male lead, who is her dad's business counselor) and women (like the old man's house maid).
Princess Agents: Chu Qiao briefly disguises herself as a man in episode forty-three. It's one of the least convincing disguises imaginable, complete with a blatantly fake moustache and beard.
Princess Silver: Rong Le dresses up as a man when she escapes Western Qi's palace, and later when she goes to see Chen Yu.
The Princess Wei Young:
- Tuoba Di pretends to be a boy for her own amusement, as well as to Troll unsuspecting strangers.
- Xin Er and her bodyguard Jun Tao dress as boys to wander around the town in the first episode.
Queen for Seven Days: Chae-gyeong is disguised as a boy when she first meets Lee Yeok.
The eponymous heroine of the Korean drama Queen Seondeok.
Amusingly subverted in The Curse of the Claw episode of Ripping Yarns (a parody of "The Monkey's Paw") with a character who appears to be an obvious Sweet Polly Oliver because her strict Victorian upbringing was so strictly Victorian she doesn't know she's a woman (or indeed what women even are.) The hero is happy to "enlighten" her.
The Rise of Phoenixes:
- Zhi Wei has to pretend to be a man for several years.
- Shao Ning makes a truly terrible attempt to disguise herself as a man while attending Qingming Academy. She doesn't even bother to remove her make-up.
In the 2006 Robin Hood a Saracen woman called Saffiya disguises herself as a boy called Djaq. It takes the Sheriff of Nottingham several episodes to guess she's a woman and (season 2 spoiler) he still hasn't pegged that "The Nightwatchman" is in fact Marian in disguise, despite the fact that the masked thief has rather conspicuous breasts.
In the Victorian sections of the Sherlock episode "The Abominable Bride", Molly Hooper's counterpart is still The Coroner, but is wearing a false moustache to do it.
In UK children's TV series Sir Gadabout (The Worst Knight in the Land) the incompetent Knights of the Round Table are regularly saved by taciturn "Sir Knight", who unknown to them, is King Arthur's young daughter, Princess Elenora (Tamsin Egerton), wearing chainmail.
An episode of Sonny with a Chance has Sonny disguise herself as a male fan of herself.
In Star Trek, Ferengi society is highly sexist, and female Ferengi are denied the right to work, do business, or even wear clothes; naturally, in one episode of Star Trek: Deep Space Nine, the plot revolves around a crossdressing Ferengi woman.
- And in another, Quark not only crossdresses but actually gets a sex change in order to seduce a businessman into supporting female enfranchisement.
- Quick note about the Ferengi: to them, not doing business is more sexist than not wearing clothes. Their hat is capitalism, after all.
Strange Empire: This is how most characters probably view Morgan Finn (the concept of being Transgender was still pretty unknown at the time), while Kat also disguises herself as a man to marry Isabella for business reasons (since same-sex marriage didn't exist then legally of course).
On the first episode of The Suite Life on Deck, Bailey disguises herself as a boy to get into Seven Seas High. Played With: The program accepts both genders, but by the time Bailey applied they were out of spots for girls. Fortunately for her, London created a vacancy by bribing her roommate to quit the program, so Bailey became her new roommate instead.
Tehran: Tamar dresses up as a male security guard to sneak into an electrical station in the last episode of Season 1, complete with a fake mustache.
Ten Miles of Peach Blossoms: Kunlun Mountain doesn't accept female disciples, so Bai Qian disguises herself as a boy to get in.
Tipping the Velvet (2002): Due to her work as a male impersonator, Nan is an expert at this. After leaving that work, she first dons a male outfit to avoid street harassment from men, then after she gets hit on by gay men keeps doing it for sex work.
In the second season of Twin Peaks, Catherine Martell, presumed dead, disguises herself as Japanese investor Mr. Tojamura. Her costume fools the other Twin Peaks residents, including her husband.
Whitechapel (TV Series): Jimmy Kray's "boyfriend" was revealed as female. She's pretending so Jimmy can be perceived as gay like his supposed father, Ronnie Kray.
We Are Who We Are: Caitlin goes out dressed as a boy several times, and seems to want people thinking she is one. As she's later also indicated to perhaps be a trans boy, it's a way of exploring that.
The Witcher (2019): Ciri is shown more than once running off outside the castle dressed as a boy to play with commoner youths.
In the '90s Fred Savage sitcom Working (1997), Chris Grant (short for Christina) shows up for an interview to join the office where the show is set. The boss is a known philanderer and "good old boy," so Christina dresses and acts masculine to get on the boss's good side and score the job. Hilarity Ensues when her gender is revealed to the main character (but not the boss), and then they all hang out in a sauna. Even more Hilarity Ensues after Chris is found out, gets fired, and the office rises up against the boss's unfair hiring practices. In the next round of interviews, he's forced to consider females for the job. The woman he chooses to hire is actually the main character in drag.
You Are Beautiful has the heroine pretending to be her teenage heartthrob brother in order to take his place in a boy band. Jeremy's reaction to her reveal is priceless.
Jacqueline, alias Jacques, a woman disguised as a man while on the run for murder, in Young Blades pleasyed by Karen Cliche. Although in her case, it's a Paper-Thin Disguise.
- One episode has an assassin using a "bending light" trick to make himself look like anyone, including "Jacques." D'artangan (who knows Jacqueline's secret) tells her he was able to realize this was an imposter as he was "too masculine."
The Young Riders: Pony Express rider Lou was really Louise, and managed to keep her real gender hidden from most of the main characters for nearly the entire first season (and from some of them for even longer.)
- Her love interest, and eventual husband in the series finale Kid, learns her secret in the very first episode and agrees to help her keep it (it's the shared secret that helps them bond together). The other riders learn it in the fourth episode, but only when they encounter Lou's father and siblings. Teaspoon learns it in the second episodes of the second season.
- Note that the Real Life Pony Express specifically recruited "small wiry fellows, preferably orphans" as riders, making this entirely possible.
In Zoey 101, Lola dresses up as Steve to prove the boys that there's no biological reason they can't act normal when there is a girl around.

Manhua

Hua Mulan is also a recurring character in the Taiwanese Yonkoma series Wulongyuan (in traditional Chinese: 烏龍院; literally "The Oolong Institute") by Ao Youxiang (敖幼祥). In her origin story, she's a natural-born badass, but too boyish and destructive (she's the leader of her otherwise all-male gang) for her parents' liking that they're actually glad that she decides to join the army and leaves home (they even pray that she won't come back). She has to put up with the antics of the main characters from Wulongyuan who are also recruited while trying to maintain her secret. After defeating the comically incompetent Hun army, she accidentally reveals her secret while getting drunk in a celebration party (because the waitress is also drunk and gets them the wrong type of drink), which turns out great because the Hun leader's actually into a strong female type. They end up married, which enables a good relation between China and the Huns. China then goes on to enlist women more often, and the main characters get a chance to goes on another fun war field trip, this time in drag. Later after she gives birth, the residents of Wulongyuan (who are now her friends) are tasked with babysitting her baby.

Manhwa

Boy Of The Female Wolf: The Hot-Blooded heroine ditched her femininity (except for the part that likes guys) after her mom left her to marry someone else and she has despised female "weakness" ever since.
He's Dedicated to Roses: The heroine is a very plain girl who becomes a very pretty boy in order to escape her Rich Bitch "owner". Somehow no one notices her huge stash of stylish male clothes despite her being a servant.
Love In The Mask: Hyu-Bin is essentially forced into being a boy in order to be an effective bodyguard for a wealthy girl the same age. While Bodyguard Crush does not ensue, even the guys think "he's" pretty.

Music

Man Man: In "Poor Jackie", the titular character is a killer on the loose who disguises herself as a man to evade the police.
Samantha Moore: "Glory Reaped" is sung by a young woman who disguised herself as a boy to enlist and win glory in battle to earn her father's pride. However, by the end, she is so horrified by the bloody horror of war that she swears off martiality for the rest of her life.
The traditional song "Jack Monroe" (or "Jack-A-Roe" as covered by the Grateful Dead):
Jackie's gone a-sailing with trouble on his mind
He's left his native country, and his darling girl behind
Oh, his darling girl behind
She went down to a tailor's shop and dressed in mens' array
She climbed on board a vessel to convey herself away
Oh, to convey herself away.
- A variant called "Lily Munro":
This girl she dressed herself all up in man's array,
And to the war department she then did march away.
Lay the Lily-o, lay the Lily-o.
The HoneyWorks song "Love@Liar" follows a young girl, inspired by the sound she heard of a particular band, disguising herself as a boy in order to join it and pursue a music career.
In the Child Ballad The Famous Flower of Serving Men, the heroine's husband and baby are killed by her mother, and she disguises herself as a man to run away and work.
In the Child Ballad Child Waters, the heroine refuses to leave the hero, despite his declaration that he goes to woo another woman. He insists she dress as a footpage and run alongside his horse.
In the Child Ballad Rose the Red and White Lily, the sisters dress as men to escape the Wicked Stepmother and rejoin with their stepbrother lovers.
At least two recorded versions ^noteJeannie Robertson's and The Pogues' of the Anglo-Irish folk song I'm a Man You Don't Meet Every Day are sung by women, turning a simple bragging song into this trope. There's also at least two female-sung recordings of Star Of The County Down, but they're less well known.
Yet another one (Robin Hood and Maid Marian) has Marian seek Robin, armed and in man's clothing, and when the two meet Robin is also disguised - so they fight, for "at least an hour or more", before recognizing each other.
Crossdressing is a classic folk music trope. One song, "The Soldier Maid," also known as "Female Drummer" (not sure whether it's true folk or modern) is about a girl who joins the British army as a drummer boy, and is only betrayed when a woman comes on to her, learns she's female, and goes off to tell her officers. The officers are actually disappointed they have to send her home, and give her a bounty and pension for her service. The song "Cruel War," covered by Peter, Paul and Mary, focuses on a woman who follows her love to war disguised as a man.
- "Jackaroe" is another song about a girl who goes off to war to follow her love, this time in the Navy.
- As is "Billy Taylor" (or "Bold William Taylor"), but it has a twist ending. It turns out that the titular character, whom the song's main character has joined the Navy to follow, has found a new girl, and the main character tracks them both down and kills them, and is promoted for it.
- "The Handsome Sailor Boy" — In which a young woman signs on a ship as a cabin boy and the captain falls in love with her. In some versions, she's looking for her lover and doesn't tell the captain she's a woman, until she's safe on shore. In others, she's just doing it for the adventure, both the captain and the captain's wife fall in love with her — but it's only the captain (and his wife in some versions) who realizes she's a woman ... Until one night, on board ship, when she gives birth. Then everyone knows.
- In "The Female Rambling Sailor", a woman goes to sea after her lover is pressed into naval service and drowns. She proves an exemplary sailor, and none of her crewmates suspect her identity until she dies in a fall from the rigging and they discover her 'female form'.
There's a Spanish ballad about a girl who dresses like a man, calls herself Don Martín and goes to war because her father is too old. Then, the prince falls for her (getting extremely confused because he somehow suspects "he" is a girl, but isn't quite sure). Then the prince comes out to the queen and she suggest several tests to expose Don Martín, all of which fail, except the last one: a bath. Don Martín runs away and the prince after her, and they marry.
Grażyna, a 1823 narrative poem written by Adam Mickiewicz features an eponymous heroine living in the 15th century, who, as a protest against her husband coming to an agreement with Teutonic Knights, secretly puts on his armour and leads the army into battle with the enemy.
- This poem is said to have inspired the Emilia Plater, a real-life military heoine of the November 1830 uprising against the Imperial Russia. Plater cut off her hair, put on a men's uniform and equipped a unit of more than six hundred volunteers - half trained soldiers and half peasants with war scythes. It's a significant fact that Plater had been also immortalized by Mickiewicz in his poem Śmierć pułkownika (The Death of the Colonel)
Spoofed in W.S. Gilbert's The Bumboat Woman's Story. The heroine disguises herself as a man to sign on as a sailor on the gunboat of handsome Lieutenant Belaye, whom she loves. When Belaye returns from leave with a wife, it is revealed that every one of the sailors on the boat is a woman who disguised herself for the same reason.
Played with in Martinmas Time, in which a girl is forced to swear she will visit a camp of nearby soldiers. She arrives dressed as a soldier and demands entrance. Impatient for the girl to show up, the soldiers tell her to hurry up and leave, even paying her to do so. At which point she reveals her disguise, ties her garter to their gatepost, and escapes.
Deconstructed in Elizabeth Barrett Browning's The Romaunt of the Page, where a lady accompanies her husband on a crusade, disguised as a page, only for the husband to declare that such an act "unwomans" a woman and that he'll only think of her as a page and never as a wife. The woman breaks down and sacrifices herself when they are ambushed by the Saracens.
Also in the different versions of Norwegian ballad Liti Kjersti Stalldreng (Little Kirsti Stableboy), where the heroine disguises herself for nine years as a stable boy in the royal stable. The prince goes Sweet on Polly Oliver, and the result reveals itself when the king finds the clever stable boy in the stable, giving birth. He recognizes the relation, and accepts Kirsti as his son's wife.
Jazz musician Billy Tipton was revealed after death to be female, which surprised everyone, including his family. He started his career during a time when it would have been very difficult for a woman to be successful, so this may have been the reason for presenting as male (though nobody is sure).
Sabaton's song "Lady of the Dark" is about Milunka Savić, a Serbian woman who passed herself off as her own brother when he was called up to fight in the First Balkan War. She was eventually discovered after she took a bullet on her tenth deployment, but she was such a good soldier her commander refused to punish her and allowed her to serve openly in the infantry through World War I; she became the most decorated female soldier in recorded history.

Myths & Religion

Older Than Print: Earlier than the Trope Namer is the original legend of Hua Mulan. This story was first recorded in the 6th century C.E.
Hervor the Elder from The Saga of Hervor and Heidrek dresses as a man and calls herself Hervard to join a group of vikings, later becoming their leader. It's not until after she has led the vikings, recovered her father's sword and ventured into a land ruled by giants that anyone works out that she is a woman.
The medieval legend of Pope Joan, supposedly a woman who disguised herself as a man to enter the Catholic priesthood and rose high enough to become Pope. Allegedly she was discovered when she went into labour during a religious occasion, and either died in childbirth or was executed for her masquerade. It was widely believed to be true for centuries, even by figures within the Church.
Another old but non-military Chinese example, the Butterfly Lovers: Zhu Yingtai, who disguised herself as a man to pursue education. She fell in love with her slightly clueless roommate Liang Shanbo and arranged to have him marry her 'sister.' Unfortunately, the villain of the story, Ma Wencai, used his wealth and power and forced her to marry him, which results in Liang becoming fatally ill out of grief and dying. In the end, some magic happened, Liang's spirit came back and took Zhu with him, and they both became a pair of inseparable butterflies. TV adaptations of the legend tend focus on the hilarity that ensues Zhu as a young woman having to live among men, how she tries to devise a way to sleep "safely" with Liang, and how Liang is so naive, borderline stupid but in an adorable way, around this oddly feminine and beautiful "best buddy" of his.
The most commonly accepted explanation for the name of Petit Jean Mountain in Arkansas is that a young French lass dressed as a cabin boy ("Little John") to be near her fiance, who was a sailor on a ship headed to the New World. She caught ill and died, and her alleged grave can still be seen on the mountain.
Older Than Feudalism: In the fourth century B.C. married women were forbidden to watch the Olympic Games on penalty of death, but a woman named Kallipateira dressed as a male trainer to go and watch her son compete. When her son won, Kallipateira somehow accidentally revealed herself as a woman while celebrating (perhaps as a Wardrobe Malfunction). Kallipateira was spared from death, however, since she came from a large family of Olympic victors, including her father, the legendary Olympic champion Diagoras of Rhodes. It is said that this episode was what started the tradition of both trainers and athletes to attend the games naked.
In a more respectable counterpart to the Pope Joan story, Theodora of Alexandria committed a serious sin and felt called to do penance by entering an all-male monastery. (She chose not to join a women's community because her husband could too easily have tracked her down.) As "Theodore," she became renowned for her holiness. When a young woman accused Theodore of fathering her unborn child, Theodora was unable to prove her own innocence without revealing her secret; she ended up raising the child. She is venerated as a saint.
Robin Hood: In one of the ballads, when Maid Marian journeyed to Sherwood Forest to find Robin Hood, she did so in disguise as a male warrior. The number of above Robin Hood adaptations where Marian does this gambit are probably drawing from this story, especially as it's one of the oldest testaments to her Action Girl status, given when she found Robin, he was also in disguise and, because neither knew who the other were, they fought for hours to a stand-still.

Radio

In Lucy Porter's Family Way, Lucy Porter laments that all she knows about her great-grandmother is her recipe for potatoes, and wishes it had been written like a modern food blog, so included lots of stuff about her life story. In this fantasy, Lucy's great-grandmother took her brother's place in the Crimean War, became pregnant by her superior officer, and married a gay man to avoid a scandal.

Roleplay

Dino Attack RPG has a strange case in that while this trope is played straight, it is not for the usual reasons, as the Dino Attack Team is clearly established to have no objection to hiring women. Instead we have Agent Pyro (who despite spending most of his time wearing a gas mask was clearly stated to be male) seemingly turning out to be a woman. It is later revealed that the woman who was unmasked was actually Pyro's estranged daughter, who had stolen his gear while he was passed out drunk and then impersonated him in order to protect him from The Mole that was killing his teammates.
Huge Schoolgirl Dacey "Dawson" Ashcroft in Survival of the Fittest pretends to be a guy due to the negative attention she received in her previous school, feeling it easier to get through highschool if everyone believes her to be a man. Luckily, she doesn't look all that feminine, and unlike some of the other female Southridge students lacks large breasts.

Tabletop Games

Since only men can be knights in the default setting for Pendragon, the game suggests this option for players who want to play female characters and whose Gamemasters are not willing to house-rule it.
In Traveller, both the Aslan and the Sword Worlders have specific rules for this. In both these cases this is not a disguise so much as a formalized way to allow vocational flexibility in females without hurting the traditions. In the case of the Aslan it comes about when there are no male heirs and a female has to "become male"; which includes not only carrying out male roles but vowing celibacy. In the Sword Worlds it is a way for eccentric women who actually want to go adventuring to do so without hurting the Stay in the Kitchen principle.
In Warhammer Fantasy Roleplay, women are forbidden from owning property or managing their own affairs in Bretonnia, so any female adventurers will have to pretend to be men. That said the opening chapter of the rulebook is very clear that the author and Black Library do not endorse medieval sexism and you have the liberty to remove these elements if you wish.
In the GURPS Robin Hood "Cyber-Robin" setting, Robyn Lincoln uses an avatar of Errol Flynn's Robin when cracking megacorps and giving to the poor, both to conceal her true identity and because she's a fan of the legend. She has no idea that the hacker she assigned the name "Maid Marian" has assumed a) that she's actually male and b) that this choice of name indicates a romantic interest, which Marian thinks she reciprocates. To make this worse, Marian is homophobic, and if she learns the truth will assume that Robyn is a lesbian (which she isn't) and was trying to "trap" her.

Theatre

William Shakespeare loved this trope. Partly because, since female actors were forbidden on the Elizabethan stage, all the young women in his stories would have been played by boys, and having them dress as boys would make it easier for everyone involved—and add to the layers of sexual confusion onstage (after women were allowed to act on the English stage in the 1660s, playwrights continued to include this as part of the plot as a form of Fanservice).
- Two Gentlemen of Verona is the first appearance of the trope in Shakespeare (since sadly he had chosen to leave his Joan of Arc out of drag). Julia disguises herself as a page and follows her beloved Proteus to Milan, helping him rescue Silvia from a band of brigands.
- In The Merchant of Venice, Portia and her handmaid Nerissa disguise themselves as a young lawyer and his clerk and follow their new husbands to Venice, where Portia intercedes in the trial of Antonio and saves his life. Portia and Nerissa are likely inspired by their friend Jessica, who earlier in the play disguises herself as a boy to elope with her star-crossed lover Lorenzo.
- Things get especially interesting in As You Like It. Rosalind is banished by her uncle, and to aid her in her travels she dresses as a young man called Ganymede. Naturally, she runs into the man she secretly loves, Orlando, who is in turn so consumed by his passion for her that he doesn't even recognize her. So Ganymede offers to "cure" Orlando of his love by pretending to be Rosalind. Got that? Male actor playing female character disguised as young man playacting young woman—in love with young man. Complicating matters, a country girl called Phoebe meets Ganymede and promptly falls in love with "him."
- In Twelfth Night, Half-Identical Twins Viola and Sebastian are separated in a shipwreck. Viola, assuming her brother has drowned, disguises herself as a eunuch and goes into service for Duke Orsino—who decides to send "Cesario" as an emissary of love to the unaccommodating object of his affections, Olivia. You can guess what happens next. And then the actually-not-dead Sebastian shows up and, of course, is promptly mistaken for Cesario. Zany hijinks ensue.
- Imogen of Cymbeline spends much of her play disguised as a young page, after being framed for adultery and fleeing the royal court.
Happens fairly regularly in Opera
- In Beethoven's Fidelio, the title character is actually a woman named Leonore, dressed as a man in order to free her husband Florestan from prison. Awkwardly, The Warden's daughter is in love with "him."
- Poor Zedenka (Arabella, Richard Strauss), forced to dress as a boy because her family cannot afford to let her doll up like her big sister Arabella. She gets her man in the end, so all is well.
- Handel's opera Alcina. Brave girl Bradamante dresses as a man, under the name Ricciardo, to save her lover Ruggiero from the clutches of the sister witches Alcina and Morgana. They both fall in love with "him." A messy love network ensues.
The plot comic opera The Firefly has pretty little street singer Nina run away from home to Bermuda disguised in boy's clothes. Unfortunately, the boy in question happens to be the notorious pickpocket Antonio Columbo.
The operetta Naughty Marietta has the title character live disguised as a boy (the son of a puppeteer) to hide from people who are trying to take her back to Naples for an Arranged Marriage.
Servant Of Two Masters has Beatrice, who sometimes wore men's clothing, disguise herself as her brother.
In Bertolt Brecht's The Good Person of Szechwan, Shen Te has to dress as her fictional (male) cousin Shui Ta, in order to get respect from her clients.
In Edward Albee's play The American Dream, Grandma reveals that she won a baking contest disguised as "Uncle Henry", lampshading that an old woman and an old man look pretty much alike.
In the musical Something Rotten!, which takes place in Shakespearean England, Bea disguises herself as a man so she can get a job, and later disguises herself as a lawyer so she can defend Nick from being sentenced to death.
The Dallas Theater Center's 2022 production of A Christmas Carol had Tiny Tim played by a girl, despite the character still being male.

Video Games

Despite appearing as an enemy, King was handled as this in the original Art of Fighting — her reason in this case being that due to not being able participate in Muay Thai tournaments as a child due to her gender, she passed herself off as male and continued to do even after moving to the United States. Later games made her femaleness more obvious, even including visible breasts — although relatively modest-appearing... despite the fact that without binding and concealment, her bust measurement rivaled Mai Shiranui's, which was capitalized on for some fanservicey official art, and occasional in-game fanservice. The King of Fighters 2001 threw this muted handling of her appearance completely out the window, but we don't like to talk about it.
- In the first game, King's gender was a Tomato Surprise that you could uncover by defeating her with a fireball attack. Too bad her hit cries were so feminine that it hardly counted as a secret.
Cocona from Ar tonelico III disguises herself as Tatsumi to avoid being detected as a reyvateil.
In Assassin's Creed it's supposed to be a surprise when, after your attempt on Robert's life, a woman takes off the helmet. Might have actually worked if, during the preceding battle, every time "Robert" was hit "he" hadn't sounded like a woman crying out in pain.
- If the player has a sufficiently tuned "babe-dar" then the player likely noticed how feminine the target was in the cut scene before the battle even commenced.
- In Assassin's Creed III some of the soldiers that wear face covering scarves make grunting sounds that imply this trope.
- Assassin's Creed IV: Black Flag features Mary Read posing as a teenaged boy^note. While she does a decent job of hiding it^note, it's pretty noticeable — for starters, she doesn't have a "James" voice — and the reveal is probably not too much of a surprise, especially if you know your history beforehand.
Kaye from Blazing Souls is an elven princess who escaped her family and dresses as a man to avoid unwanted attention, working as a bodyguard for Bridgette. She's caught changing clothes by Zelos of all people, and he's nice enough to keep the secret for her.
Sypha Belnades in Castlevania III: Dracula's Curse. Being a witch, she had to disguise herself to avoid being burned. The game and manual were fairly good about concealing this fact until the very end. Her doppelganger in Castlevania: Symphony of the Night, however, is feminine right from the get-go. And then Castlevania: Judgment gives her large breasts and a fanservicey outfit. Finally, in Pachislot Akumajo Dracula III, Sypha wears a garb similar to her original look (but with more of an emphasis on her womanly attributes) and is frequently seen with her hood down, similar to her zombie doppelganger in SotN and Portrait of Ruin.
Cute Bite: When at balls, the vampire protagonist does this so she can I Kiss Your Hand to bite ladies and feed herself.
In Da Capo, Kanae Kudou is disguised as a boy due to her strict traditional upbringing, mainly that she's not allowed to flirt with boys. So much that she already had to transfer schools once when her identity was found out.
In Dragon Force, one of the leaders is a female who wears intimidating and bulky armor with a face-concealing helmet for the first half of the game. Her proper gender is indicated immediately if you play as her in the campaign, but nobody else knows until she takes off the helmet.
In The Elder Scrolls backstory, Barenziah, the future Queen of Morrowind, ran away from her Imperial loyalist foster family as a teen by disguising herself as a boy. She continued to pose as a boy for some time after in order to avoid detection.
In Fantasy Life, Princess Laura, who is first met in her boy disguise.
Final Fantasy:
- Faris from Final Fantasy V. Yes, "his" secret is outed very early on, but she doesn't start dressing any differently... apart from two or three of her jobs, including the Mystic Knight and the Dancer, both of which only become available after The Reveal. It's also worth noting that she still talks like a man and is clearly uncomfortable the one time she's shown wearing women's clothing.
- In Final Fantasy XIV, it's eventually revealed that Nael van Darnus is a woman under the helmet when the world knew her as a man. Encyclopedia Eorzea would explain that this is Eula Darnus, Nael's sister. Eula Darnus idolized her brother, but he tragically died in a military campaign due to his father's poor leadership. Eula would wear her brother's armor, use a voice modulator to disguise her voice, then killed her father and anyone who knew of Nael's death to impersonate him and strive to build a lasting legacy for his name.
- A bug (maybe?) actually creates one in Final Fantasy Tactics. The first stage of the Deep Dungeon/Midlight's Deep occasionally spawns a "male" Time Mage... who screams like a girl, literally. If Invited into your party, you'll discover that she's actually a female unit in everything but in-battle appearance; she can use female-specific equipment and can access the Dancer class (but takes on the appearance of a Bard when she does), and she is susceptible to Steal Heart from male units (and, if taught the ability, can use the same skill on them). She even gets female sprites in the formation menu; just not in battle.
In Fire Emblem: Awakening, when Lucina comes from the future to save her father in her attempts to stop the Bad Future, she disguises herself with a Cool Mask concealing her eyes (which have a Brand that would reveal her identity) and tucks her hair into to assume a boyish appearance and goes by the pseudonym of "Marth". Eventually, she reveals her true gender after her mask is broken while averting an assassination attempt on Chrom. It is also suggested that Lon'qu, a warrior fighting in the tournament at Ragna Ferox, lost to "Marth" because even though he was the more skilled swordsman, his realization that "Marth" was a woman caused him to lose his edge due to his trauma-induced gynophobia.
Shiva in the first Galaxy Angel game is made to crossdress for political reasons.
In Genji: Dawn of the Samurai, Otohiko is actually Lady Shizuka, despite players never hearing Otohiko's voice and the game continually referring to Otohiko as a "he." She did it to avoid the enemy Heishi's pursuit.
Leucos in Glory of Heracles (DS) tries this to escape from authorities, but she doesn't pull it off well, and the game's characters (and even the tutorial) Lampshade this.
Jade Empire features a theatrical production in a culture where only men may be actors; naturally, if the player character is female, she takes the part anyway. Of course, it's a female part...
Gaol in Kid Icarus: Uprising dons the Dark Lord armor, which even makes her voice deeper. While Magnus already knew her from before, Pit and Palutena are fooled until her armor is broken.
In the video game The Legend of Zelda: Ocarina of Time Princess Zelda disguises herself as a warrior named "Sheik" to hide from the main villain and help the main hero. The reveal was a big surprise to players when the game first came out, but now it's so well known you can even have her switch back and forth between the two personas in the first three Super Smash Bros. games.
- However, whether Shiek is actually male (or meant to be perceived as male) is hotly debated amongst fans. The non-canon manga adaptation of OoT says that Zelda magically gave herself the mind of a boy, while Super Smash Bros. and Hyrule Warriors present the Sheik disguise as more overtly female-looking and use feminine pronouns. Ruto briefly refers to Sheik as a "young man" in the only time Sheik and their gender are mentioned by another character in-game, but the two never directly interacted with one another, so it could be that Ruto was mistaken. Ultimately, Ocarina itself is ambiguous about whether Sheik is merely a female disguised as a male as per this trope, a male who was transformed from a female, or a female whose disguise is also meant to be female, though most spinoff material leans towards the latter.
The Lion's Song: After being humiliated when presenting her thesis to The Radius, an all-male mathematical society during 1900s-1910s Austria, Emma disguises herself as a man to get membership and present her theory.
Metal Gear
- A common trope in the early games (particularly in Metal Gear 2: Solid Snake, Metal Gear Solid, and Metal Gear: Ghost Babel) had Solid Snake having to rendezvous with a female ally who has already infiltrated the enemy by disguising herself as a soldier. Particularly in MG2 and MGS, the only way to determine who is Snake's contact is to follow said contact to the Ladies' room. Or if the player is detail-oriented, they may notice that the actually-female soldier sways her hips as she walks, and has slender legs. Snake himself notices it, a fact which is later given a nod in Super Smash Bros. Brawl when he realizes immediately that Samus Is a Girl.
- In Metal Gear Solid 2, Olga Gurlukovich disguises herself as a Cyborg Ninja similar to Gray Fox from the first game, while disguising her voice and using the alias of "Mister X."
In the obscure Sierra adventure game Pepper's Adventures in Time, the titular character disguises herself as a boy for about 90% of the game, considering that she time travels to the American Revolution.
Mortal Kombat: Deception: Before getting recruited into the new Black Dragon, Kira sold weapons to terrorists while disguised as a man until her cover was blown.
Naoto Shirogane of Persona 4.
- Also, Izanami is disguised as a male gas station worker.
The player character of Queen at Arms has been raised as a boy and given a boy's name for as long as she can remember, but she knows perfectly well that she's a girl. Her adoptive family did this to conceal her true identity, for very good reasons.
In Rival Schools, Akira goes undercover in a body-concealing motorcycle helmet and leather jacket to investigate her older brother's disappearance. This is necessitated by the fact that her brother attends an all-male school for delinquents.
Rhythm Thief: Charlie, though it's never made clear if she intentionally tries to look like a boy or not.
Shantae and the Seven Sirens: A woman is disguised as a man to avoid her enemies, as revealed right before the end of the game. It's Risky Boots as the Arena Town Mayor.
In Star Wars: The Old Republic, it's revealed at the end of the Imperial Agent storyline that Hunter, the Agent's Arch-Enemy is actually a woman wearing a holographic disguise as part of her cover. If you're a male, she'll even claim that she's fallen for you, giving you the chance for a Last Kiss.
Flash game Star Wish has one. Figure it out.
In Tears to Tiara 2. At one point the party decides to let themselves be captured by slavers. The girls disguised themselves, with some magical help, so they will be kept on the same ship as the guys.
Jayle, one of the Einherjar in Valkyrie Profile is a woman disguised as a male soldier. Interestingly, her commanding officer discovers this, but keeps his mouth shut because they've fallen in love with one another. She's more conspicuously outed just before her death, when a sorceress's seduction spell, fails to entice her. It did however entice that commanding officer, who runs her through.
- Much like Faris from Final Fantasy V, in battle she continues to dress the same and is acknowledged as her soldier persona for all intents and purposes.
Inverted in The Witcher 3: Wild Hunt. You overhear a group of drunk soldiers telling a story about a farmer who had disguised his Pretty Boy son as a girl to hide him from the war. The punchline to the "joke" was that the soldier tried to rape the "girl" and on discovering their real gender, went ahead with the rape anyway. You can practically hear the disgust in Geralt's head.

Visual Novels

In The Great Ace Attorney 2: Resolve, the main character's assistant Susato Mikotoba disguises herself as a male defense attorney to defend her close friend Rei Membami, under the name 'Ryutaro Naruhodo' (registered as such by her father).
In Fate/stay night, Saber is actually King Arthur, or rather Artoria Pendragon, who passed off as a boy thanks to Excalibur, which maintains her youthful state.
Galaxy Angel: Shiva, though only in the first game, is assumed to be a young boy for the most part of the story. It is possible for Tact to learn her true gender, and she explains that the reason her gender was concealed was for her own protection. From the second game onwards, however, this trope no longer applies as she publically reveals herself as a girl after she takes the empire's throne.
In Hakuouki has protagonist Chizuru Yukimura dress as a boy to go looking for her father after he goes missing due to laws that prevented women from traveling alone and to make herself less of a target in Kyoto. After moving in with the Shinsengumi, Chizuru is asked to maintain the disguise to prevent an issue about a woman living in the compound. Key members of the Shinsengumi are informed of the truth early on and others see through the disguise later, but it was passable enough that one of Chizuru's love interests gets Mistaken for Gay.
Jack Jeanne: One of the conditions that Kisa has to accept in order to be enrolled and succeed in Univeil is that she has to disguise herself as a boy, and that no one should know of her true relation with her brother. Given that it's an Otome game, that doesn't stop the love interests from falling in love with her.
Lady In Mystery has Heesoo, a young woman who is the daughter of a man convicted of treason. She dresses up as a man not only to hide her identity, but also to make running a detective agency easier.
Phoenix Wright: Ace Attorney – Dual Destinies has Robin Newman. When she's revealed to be a girl, she keeps switching between a very girlish personality and the boisterous, masculine personality she was using before.
Professor Layton vs. Phoenix Wright: Ace Attorney has Jean Greyerl, who lived as a boy to hide the fact that she was a witch.
Shall We Date?: Ninja Shadow has Saori Shishido, a bifauxnen Player Character whose girly-looking twin brother Kaname, is murdered. She then takes up his identity and rooms in with an all-male Vigilante Man group that her brother was supposed to join (who are totally not a ninja version of The Shinsengumi), determined to punish his killer and get help from the Vigilantes for her and Kaname's village, which is going through hard times. Her disguise is actually good enough that the Vigilantes often ask her to dress up as a girl because they believe she's a girly-looking young man.
Rei Ijuin in the original Tokimeki Memorial because apparently her father wanted a boy.

Web Animation

TOME has an interesting example with Gamecrazed. Because it's a video game, hypothetically anyone could simply Cross Play to pull this off. However, the only character to actually do something similar is SOFDTI (an artificial intelligence), who technically didn't have any gender to begin with (but identifies herself as female). When she creates a digital avatar to play the game herself, Gamecrazed is mistaken for a male by Nylocke and SOFDTI saw no reason to object.

Webcomics

Dungeons & Doodles: Tales from the Tables: Before sneaking on board a pirate ship in search of her mother's killer, Angela cut her hair short and wrapped cloth around her chest to hide her breasts in order to pass off as a young boy in a crew full of male, grown-up pirates, although the captain sees through the disguise anyways since she is female as well.
Kevin & Kell: In one storyline, Kevin's dad is in debt to the Bovine Mob, led by a longhorn bull called "Mr Castrato". At the end of the story the police move in, only to find Castrato's jacket and horns abandoned ... "he" was actually a cow.
Rascals: In order to keep her promise with Jazmin's feelings, Shiro disguises herself as a man. It is revealed on this page here.
Sandra on the Rocks: Eloise, as part of a convoluted revenge plot, infiltrates a high school along with her girlfriend Nadine under the guise of two new students. She wasn't happy to find out that Nadine, for her own amusement, gave her a male fake identity.
Sticky Dilly Buns has a minor case when Ruby, basically The Ingenue, deconstructed, disguises herself as "Rudy" (basically a joke White Gang Banger), in order to assist with one of Dillon's Zany Schemes. It's a short-term effort and not a very convincing disguise (although it fools Ruby's sister during a brief encounter), but it perhaps helps Ruby's confidence, as she claims that some of Rudy rubs off on herself.
In Storm, Eolill often disguises herself as a man to be taken more seriously as a fighter.
In Strays, Meela's brother cut her hair so they could pass as brothers, rather than the brother and sister their enemies were looking for. She didn't like it.
Tiger, Tiger is about Ludovica, a young woman who steals the identity of her twin brother to take his place as captain of a ship to seek adventure and fulfill her dream of studying sea sponges.
Subverted in TwoKinds with Natani. She dresses and acts like a guy because part of her soul had to be repaired with a piece of her brother's soul. That included the part about gender identity. As a result, she honestly identifies as male even though she is in a decidedly female body. She keeps her breasts bound and disguises her scent so nobody but a trusted few know the truth.
Emet from Warrior U dresses as a boy so that she can learn to become a warrior.
What's New? with Phil and Dixie: Timothy Peter Hugo Stanley. "A few crewmembers are convinced he harbors some deep secret, but... it remains a mystery." Beneath is an obvious picture of a (not-very-Foglioesque) girl.
Spoofed here in The Whiteboard by Sandy, in response to a customer insisting on talking to one of the guys at Doc's paintball shop.

Web Original

The main character of this story in the Livejournal-based "webzine" Imaginary Beasts.
Whateley Universe: As per Word of God: Mr. Magic's son 'Artie' is actually 'Gwen'. He had an affair and she got pregnant, she broke off the affair out of concern 'about raising a child in the unstable life [he] led'. When he saw his child, "for some reason, possibly involving Gwen's tomboyish appearance, he mistook her for a boy. Seeing how elated he was in having a son, she decided to play along and—for some reason—her mother also went with the charade, both telling Mr. Magic that his daughter was a boy."

Web Videos

AFK: Maybel pretended to be a guy in the game, so she could escape being harassed and hit on.
In Video Game Confessions, Zelda often goes around in her Sheik disguise, explaining that she feels more free pretending to be both male and a commoner. Gets weird when Link starts hitting on her while she's in disguise.

Western Animation

Mizu, the titular Blue Eye Samurai. When she was a child, this was because the bounty on her head was for a girl. Now she does so because of the limited options for a woman traveling through Edo-era Japan on a Roaring Rampage of Revenge.
Clone High: The Joan of Arc clone disguises herself as "John Dark" ("Jeanne d'Arc") to join the hoops team, to give them a fighting chance against their rivals. The whole thing backfires when Abe hates John, and so in respect of Abe, "he" keeps passing the ball to him, even though "he" could probably score "himself"; so they end up being pummelled again, and don't even score until the last second of the game... which fortunately helps the principal win a bet.
- The whole thing is mocked in a leaked production piece; apparently a future storyline had Joan becoming prom queen. The position of Prom King was given to basketball star John Dark. She ends up awkwardly dancing by herself during the prom royalty dance.
- This is actually based on her historical actions, although the real Joan made no secret of her gender and wore male clothing just because it was more practical.
  - Although it's a pretty safe bet that the real-life Joan's army had no dolphins disguised as people.
By day Cybersix disguises herself as a male high school teacher.
Sam(antha) in Danny Phantom briefly disguises herself as a boy to trick three female ghosts who have made all the men disappear. Her presence was to get the three to use their powers so Sam's team could counter with their own weapon to restore all the men back.
Combined with You Go, Girl! on Doug when Patti tries out for the softball team.
An episode of The Fairly OddParents! revealed that Trixie Tang regularly disguised herself as a boy so she could buy comic books anonymously.
In Family Guy, one Cutaway Gag has Peter Griffin spending fifty years pretending to be a woman, posing as a nun, and taking care of orphans at a Catholic Mission. A French Woman wrote a documentary about it called "Mère Bernadette: Transvestite Child of God" and it won the Palme d'Or at Cannes and the Silver Scissors at the Bulgarian Lady-Weiner Festival.
In the Futurama episode "War Is the H-Word", Leela disguises herself as a man named "Lee Lemon" in order to join the army. Apparently, Zapp Brannigan has caused so many sexual harassment lawsuits that women can't join anymore. He's still Sweet on Polly Oliver.
Zapp: [after the Leela feminine reveal] I've never been so happy to be beaten by a woman!
An episode of The Grim Adventures of Billy & Mandy has Mandy disguising herself as a boy calling herself Manfred to help out Billy's baseball team which does poorly, as he wouldn't let her join because he doesn't want a girl on his team despite Mindy leading the team that always beats them. She only wears pants and a baseball cap, but once she takes off the cap he recognizes her and kicks her out only to accept her again when she puts the cap back on (he's pretty stupid).
Gummi Bears — Princess Calla does this to avoid getting a bodyguard. Her father finds out and so is impressed at how formidable she is that he immediately agrees that she doesn't need one.
An episode of Jimmy Two-Shoes had Heloise disguise herself as a boy in order to see a list of "Guy Stuff" that Jimmy and Beezy wouldn't let her see.
In The Loud House episode "Cover Girls", Lori disguises herself and covers for Lincoln when she talks to Pop Pop.
In Mummies Alive!, the main character of Nefertina spent years in ancient Egypt posing as 'Nefer' to drive chariots; according to her, only Prince Rapses knew the truth, but it is quickly exposed to the other three Guardians when they are awoken in the present day.
In The Mummy: The Animated Series, Alex's friend Yanit turns out to be a girl. Her family have been Medjai for thousands of years, and she didn't feel like breaking the tradition just because she didn't have a brother.
My Little Pony: Friendship Is Magic: In the episode "Gauntlet of Fire", dragon princess Ember disguises herself as a male dragon to compete in a Death Course, even faking a deeper voice when forced to talk. However, it is downplayed to an extent, since it's not that female dragons weren't allowed, but rather that she did not want to be recognized after her father explicitly told her not to compete.
The Powerpuff Girls (1998): In "Bubble Boy", after capturing and imprisoning Boomer, the girls disguise Bubbles as Boomer and plant her among the Rowdyruff Boys in order to trick them into getting captured.
The Simpsons: In "Girls Just Want To Have Sums", Springfield Elementary becomes segregated by gender. Since the girls' school isn't teaching math properly, Lisa disguises herself as a boy in order to join the boys' class.
TaleSpin has a gender inversion - Higher for Hire's business is suffering because its boss is female, so Baloo decides to enter an air scavenger hunt. In order to do so, he needs someone to sponsor him, but only an all-female aviation club will sponsor Higher for Hire, so he disguises himself as a lady.
In Voltron: Legendary Defender, a First Few Episodes Spoiler is that Pidge is actually a girl who joined the Galaxy Garrison to look for information about her missing brother. "Katie" had already been caught snooping, so she cut her hair and created a male identity to hide better.

Real Life

During the American Civil War, some of the corpses of fallen men were discovered not to have been men at all. At least 240 women are known to have served in the ACW disguised as men, as you can read about here Several maintained their disguises after the war in order to qualify for pensions. ^note It was a lot easier for women to get away with this back in the days before routine physical examinations, since often the only physical standards enlistees had to meet were "upright and breathing". Also, many 18^th and 19^th century women were relatively small-breasted due to inadequate nutrition, and many figured out the trick of padding out their waists instead of trying to completely eliminate their breasts, which was often helped by ill-fitting uniforms and the sartorial customs of the time, which required several layers of relatively thick and unyielding fabrics and often resulted in people resembling unmade beds.
Joan of Arc did not disguise herself as a man, but chose to wear men's clothing while fighting for practical reasons. ^note
Deborah Sampson disguised herself as a man named Robert Shurrleff ^note and served in the Continental Army under General George Washington from 1782 to 1783. She was caught by a doctor after getting shot in the shoulder, and was honorably discharged due to her heroism on the battlefield. Deborah allowed her story to become public and gave lectures about her experiences in war until she died in 1827.
There are at least 22 documented cases of women serving in the Prussian army during the Napoleonic Wars. They include:
- Eleonore Prohaska (1785-1813), who served as private August Renz in the Lützow Free Corps and only revealed her real identity when she was mortally wounded in the battle of the Goehrde (1813).
- Louise Grafemus (1786-1852, born Esther Manuel), a converted Jewish mother of two, who served with some financial backing from Princess Marianne of Prussia as an uhlan during the Wars of Liberation (1813-1815), searching for her husband who, as it turned out, was serving in a Russian unit and was killed before the war ended. Grafemus lost her right hand, was promoted to Wachtmeister (sergeant-major) and was decorated with an Iron Cross. After the war she moved to St. Petersburg, married a second time, and as the widow Louise Kessenich ran an inn called "The Red Zucchini".
- Friederike Krüger (1789-1848) alias August Lübeck served in the Kolberg Infantry Regiment from 1813 to 1815, rose to Unteroffizier (sergeant), and was awarded an Iron Cross and a (Russian) Cross of St. George after being wounded and discovered to be a woman at the battle of Dennewitz in 1813. After the 1815 campaign she retired from the military, married another Unteroffizier, and had four children.
- Maria Werder, the wife of a landed gentleman, served as a hussar to be with her husband in the campaigns of 1806/7 and 1813. She was promoted to Wachtmeister in the 2nd Silesian Hussars and and revealed her real identity only when she left the army after her husband was killed in the battle of Leipzig.
British military surgeon James Miranda Barry (1789[?]-1865), who rose to the position of Inspector General in charge of all military hospitals, was discovered after death to have female sexual organs. Considerable historical controversy continues as to whether Barry was a trans man, or simply cross-dressed to pursue a career that a woman then could not have, and barring breakthroughs in spiritualism we're unlikely to ever get an answer that will be convincing to all.
Thérèse Figueur, the original Madame Sans-Gêne before Victorien Sardou reused this nickname for Catherine Lefebvre, served from 1792 to 1815 as a cavalry trooper and was wounded and captured a few times.
Nadezhda Durova (1783-1866), the Cavalry Maiden of The Napoleonic Wars, first served in 1806 disguised as "Aleksandr Sokolov". Her distinguished career continued after her true gender was discovered, and as a lieutenant in the Mariupol Hussars became the first Russian female officer. She later wrote memoirs of a quality that impressed Aleksandr Pushkin.
Evdokiya Zavaliy (1924-2010), the marine corps officer of World War II. She joined the Red Army as a girl in 1941 after her village was taken by German landing force and worked as a nurse. Later, she was commissioned because of injury and put in reserve regiment. When some officers came to get volunteers for the front-lines, they mistook her for a man (helped by her documents saying "Evdok.", which can be the beginning of both Evdokia and Evdokim). She decided to play along and soon became a platoon commander. After her real gender was uncovered 8 months later (as usual, in a hospital) she was sent to the officer courses and became the one and only female Marine corps officer in Soviet history. She retired in 1947 as a guards colonel. She and her marine platoon was so feared by Nazis that they called her Frau Schwarzer Tod (Miss Black Death).
During the French Revolution farmer's daughter Renée Bordereau (1770-1824) lost several relatives to the Terror and and saw her father killed before her eyes. Dressed as a man (not that hard, apparently, as she was described as very ugly) she fought in the wars in the Vendée on the royalist side under the nom-de-guerre Langevin (i. e. "the Angevin" or "man from Anjou") and was wounded several times. Since the forces of the Republic and Empire kept looking for a man, she managed to evade capture after the Vendéans' defeat until 1809. At one point she was accused of raping a girl, but was able to prove her innocence by revealing her gender, but not her real name. Imprisoned on the Mont-Saint-Michel, she was liberated after Napoleon's abdication, following which she dictaded her memoirs before taking to the field once more in the war of 1815.
As per the Assassin's Creed IV: Black Flag example, Mary Read and Anne Bonny, two Sweet Polly Olivers on the same ship, no less! Apparently the practice of women joining pirate crews disguised as men was common enough for Black Bart to specifically forbid it in his formulation of the pirates' code. Ironically, both escaped hanging because they claimed to be pregnant, since it was a pretty standard way of forestalling a death sentence, as there wasn't any immediate method to definitively confirm the allegation. Read later died of a fever while in prison, while Bonny disappeared from the record.
- Not to mention that Bonny was hitting on Read, and ended up being the victim of an Unsettling Gender-Reveal, after which she revealed her own disguise to Read.
- Read went on to fight a duel to save another (presumably) male pirate she was interested in. She allegedly won the duel by tearing open her shirt and then skewering her opponent while he was distracted.
Mollie Bean, who is known only from an 1865 article in the Richmond Newspaper, after she was discovered. She served in the 47th North Carolina Regiment disguised as a boy for over two years. Was included as a character in Harry Turtledove's The Guns of the South.
Also Catalina de Erauso, "The Lieutenant Nun".
Mexican female writer Sor Juana Inés de la Cruz, back in the 17th century, crossdressed in order to sneak into an university back when women were not allowed to receive education. She later decided to become a nun and spare herself from The Reveal.
The book Female Tars: Women Aboard Ship in the Age of Sail by Suzanne J. Stark gives several examples of women who joined the British Royal Navy in disguise (as well as exposing a few frauds). Includes a detailed autobiography of Mary Lacy, who served as a seaman and shipwright for twelve years.
Norah Vincent posed as a guy for one and a half years, exploring the male-only parts of the society (including a Catholic cloister) out of pure scientific interest. Nobody guessed that "he" was a she the whole time, however the monks began to believe that she was gay (correct but not in the way they thought)
Charlotte "One-Eyed Charley" Parkhurst, a stagecoach driver during the Gold Rush, who wasn't publicly outed until after his death.
Milunka Savic, a Serbian war heroine from World War One, was a rather awesome subversion of this trope. She joined the Serbian Army during the Second Balkan War in the place of her brother after he was drafted, and served with distinction until she was wounded in combat and her gender was revealed to the attending doctors. Her commanding officer wanted to transfer her to the nursing division, but she responded that she only wanted serve as a combatant. The officer said he'd think it over; one hour later he granted her request. Yes, she was such a bonafide badass that the military literally couldn't waste her as nurse. According to some sources, her subsequent career in WWI may have made her the most decorated female combatant of all time.
Rhian Sugden, British glamour model, disguised herself as an old man as part of The Sun’s publication to experience life in disguise. This included a convincing latex face mask and concealing her body under a sweater vest, jacket, and pants. Many were convinced this was an old man, until they heard her speak. According to the article, this was the same makeup artist who also worked on Suspiria (2018).
It's common in Afghanistan for mothers with no sons to dress young girls as boys to escort women of the family and support the family. Mothers with no sons are often pitied, and having what looks like a boy in public improves their image. Then the "boys" suddenly have to become wives, without knowing any domestic skills or even how to wear a burqa...
There have been wild rumors that the Sengoku Period warlord Uesugi Kenshin was a woman masquerading as a man. Sengoku Basara and the live-action drama Fūrin Kazan reflect this by depicting Kenshin as apparently male but beautiful and androgynous.
Let us not forget Hatshepsut, Egypt's female King. (And Cleopatra, for that matter, who often wore a false beard and dressed in male clothing.)
This used to be common in the Royal Navy. So common that chiefs would regularly shout Show Some Leg to make sure a given sailor was male before sending him to work.
After the Battle of Trafalgar a naked woman was found floating in the wreckage by sailors of HMS Pickle. They chivalrously gave her some clothes and listened to her story. She was sailing with her husband in disguise aboard the French ship Achille. When her ship caught on fire she removed her clothes and jumped overboard. She swam toward some shipwrecked clinging to a spar. When they kicked her off she floated in the water until she was picked up by the British.
Jeanne Baret, the botanical assistant, housekeeper, and possible lover of the French naturalist Philibert Commerçon, accompanied her master when he joined the Bougainville expedition; since women were not allowed to serve on French ships, she traveled in disguise under the name of "Jean Baret". Commerçon pled ignorance when the deception was revealed.
There was also half-legendary Polish student, Nawojka, who attended Jagellonian University disguised as a boy. She was discovered and removed from the university (though not charged with anything specific), but eventually went to a convent and became a teacher there. Her story was supposed to happen in early 15th century.
Some French officers during the Napoleonic Wars, most notably Marshal Masséna, had their mistresses dress as staff officers so that they could accompany them on their campaigns, although the disguises were often rather thin.
In the earliest days of the Boy Scouts organization, girls who wanted to participate occasionally dressed in their brothers' clothing and came to meetings under male aliases. This largely ended when the Girl Scouts were founded, although some Sweet Polly Oliver scouts maintained the ruse long enough to finish scoutcraft projects in progress.
Japanese has a surprisingly simple word for this, dansou (男装). It's also common for all-female acting troupes to have women who play boys' roles, often only boys' roles. In these cases, the actress may even appear as a man in public, despite being a woman, because it's "easier" for her fans to see her as a him (even if her gender is an Open Secret).
- The otokoyaku (male role actresses) of the Takarazuka Revue, while employed by the company, mostly dress in male-coded clothing in public. As the name implies, they play male roles of all ages, though some actresses are occasionally cross-cast as specific types of women characters that "require" the otokoyaku charm and specialty. Young boys and preteens sometimes are played by musumeyaku (female role actresses), making them Polly Olivers. Musumeyaku are stereotyped by the company as being pure and innocent - if a woman is a villain, she is almost always played by an otokoyaku -, adding to the Children Are Innocent trope.
Aliki Diplarakou was a Greek beauty contestant who sneaked into Mt. Athos, an autonomous region run by Orthodox monks that forbids the entrance of women and female animals, by disguising herself as a man.
According to the letters of an Austrian envoy in 16th century Ottoman Empire, an older woman met a younger lady in a public bath whom she fell in love with. When she was unable to successfully court her, the older lady disguised herself as a man, moved into a house next door to the younger lady, then asked her father to become her "husband". When the older lady was taken to court when her fiancee inevitably found out that her groom was female, the judge laughed his ass off at her defense, then had her taken off to be drowned at sea.
In 1785, a Russian Cossack woman named Tatyana Markova didn't want to get married, so she faked her suicide and ran away to join the army under the last name of Kurtochkin. Her service was smooth and she rose to the rank of Captain, but then a girl who failed to woo "him" accused the officer of seducing her. Markova was forced to confess the secret to Catherine the Great herself, after which the case was closed, but the officer was forced to accept an honorable discharge.
In The Lord of the Rings: The Two Towers, the majority of the Riders of Rohan were played by women with fake beards. It was decided early on that the Riders should be played by experienced equestrians with their own horses, but the modern-day horse industry is dominated by women, and in a smaller country like New Zealand, production quickly ran out of male riders. So they hired what men they could and the rest were women in drag.
Like the Trope Namer, Nguyễn Thị Bành dressed up to join the Vietnamese army and fight Chinese Ming invaders. She wowed the troops (and General Nguyễn Chích, who was actively recruiting for the resistance) by being a small, delicate, student-like "young man" who laid waste to Nguyễn Chích's best soldiers in hand-to-hand single combat, and was promptly accepted into the army. She was rumbled when the General observed her, got suspicious because of "his" feminine manners, and ordered a wrestling contest (which meant the men would have to strip down). Cornered, she admitted her identity. Instead of getting mad, expelling her, or worse, the General married her and made her his second-in-command. They eventually became a Battle Couple in the Lam Sơn resistance, trained an "army" of messenger pigeons together, and Nguyễn Thị Bành (plus a mere 60 men) once staged a daring rescue of her husband and his soldiers when they were surrounded by the enemy in the dead of night.

Sweet Polly Oliver

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Battling at Full Volume!

Alternative Title(s): He Is A She, Disguised As Male

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Sweet Polly Oliver

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Examples:

Video Example(s):

Battling at Full Volume!

Alternative Title(s): He Is A She, Disguised As Male

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Battling at Full Volume!