History Main / Crossdresser

Distinguished from DragQueen, which tends to be strongly associated with gay men and has an inherent aspect of "performance." Also ''not'' to be confused with UsefulNotes/{{transgender}}, which describes people who identify as a different gender from that which they were assigned at birth. There's always potential for overlap, however. A drag queen may ''also'' dress as a woman while "offstage", and thus be a crossdresser as well. Some people may start out as "merely" crossdressers, only to eventually discover that they are transgender.

* ''WesternAnimation/LooneyTunes'' mascot Bugs Bunny has crossdressed as a woman in nearly ''every'' incarnation he's been in. While the effectiveness of his looks [[PaperThinDisguise tends to vary]], he often pulls off the personality of a women really well.

* ''{{Film/Colette}}'': Missy. She is never in anything except men's clothing, even for sleeping wear. While this would not be considered a big deal now in Paris, it was highly controversial then.

Distinguished from DragQueen, which tends to be strongly associated with gay men and has an inherent aspect of "performance." Also ''not'' to be confused with {{transgender}}, which describes people who identify as a different gender from that which they were assigned at birth. There's always potential for overlap, however. A drag queen may ''also'' dress as a woman while "offstage", and thus be a crossdresser as well. Some people may start out as "merely" crossdressers, only to eventually discover that they are transgender.

* Kei Shimura of ''Manga/HighSchoolNinjaGirlOtonashiSan'' doesn't crossdress out of any desire to be seen as female, nor with any true villainous intent. He only does it because femininity is the only area in which he can surpass his rival, the title character Fuka Otonashi.

* ''Manga/CityHunter'': Ryo crossdressed a few times, usually to disguise himself (he can even make his Gag Penis disappear if someone checks his gender!) but, one time, he was trying to not be outed as City Hunter and faked having a job in a gay pub...
* Kazuya Shiranami of Galaxy Angel is stated as having been forced to crossdress before he joined the Rune Angel Wing. In the first game of the Galaxy Angel II trilogy, in what becomes Natsume Izayoi's route, he finds himself forced into it once more, as a maid with Grade A ZettaiRyouiki. This situation piques the curiosity of Anise Azeat when she sees him (as both Kazuya and the crossdressed Katherine, on separate occasions) sneaking around; it's in a scene where the female Angels are undressing that Lily finally busts him.

* Fanfic/KhaosOmega is known to implement scenarios that involve crossdressing, one of them a tweaked case of Kazuya's crossdressing in the first game of the Galaxy Angel II trilogy. Here, the tweak is that Lily tries a longer-range approach to remove Kazuya's maid attire but botches it; a far bustier Anise, who had seen it coming, convinces Kazuya to resume crossdressing, which he does more passionately. Anise herself is later revealed to be the primary Alpha of a massive harem whose leader, Jet Brazie, has a special gender status allowing him to crossdress without it being identified as such (he doesn't go fully until 2550 following the capture of Tracy Dennis), which Kazuya (his role in triggering Anise and Jet's marriage without an actual wedding, due to buying Anise her FairytaleWeddingDress), Jace Davies (a transformation-induced Chaos Reaction near his own Anise), and Jayden Omega (a sixth birthday present) also obtain. Jet's case is later replicated by a Cloud Strife who had previously met Anise during her [[VideoGame/SuperSmashBrosUltimate World of Light mission]], in which he'd been one of five [[Rule34 caught up in the shenanigans of Anise's then-problematic Meme Storm]], but switching elemental affinity from Ice to Lightning (presumed to be one of the decisions that result in [[ContrivedCoincidence the second convenient naming chain regarding a second-generation member of Anise's Amethysts]].

** ''Series/DickAndDomInDaBungalow'', including Mr Richard [=McCourt=] dancing the tango in a [[https://www.youtube.com/watch?v=06szyd9ccOQ&t=5m50s very fetching dress]].

* In ''VideoGame/TheLegendOfZeldaBreathOfTheWild'', [[spoiler:Link has to crossdress in order to get into Gerudo Town, a town in which men are forbidden.]]

* Never shown but there are a few jokes in ''WesternAnimation/TheWeekenders'' that imply Carter crossdresses.

* KhaosOmega is known to implement scenarios that involve crossdressing, one of them a tweaked case of Kazuya's crossdressing in the first game of the Galaxy Angel II trilogy. Here, the tweak is that Lily tries a longer-range approach to remove Kazuya's maid attire but botches it; a far bustier Anise, who had seen it coming, convinces Kazuya to resume crossdressing, which he does more passionately. Anise herself is later revealed to be the primary Alpha of a massive harem whose leader, Jet Brazie, has a special gender status allowing him to crossdress without it being identified as such (he doesn't go fully until 2550 following the capture of Tracy Dennis), which Kazuya (his role in triggering Anise and Jet's marriage without an actual wedding, due to buying Anise her FairytaleWeddingDress), Jace Davies (a transformation-induced Chaos Reaction near his own Anise), and Jayden Omega (a sixth birthday present) also obtain.

* ''Series/FatherBrown'': The VictimOfTheWeek in [[spoiler:"The Missing Man"]]. His crossdressing actually leads to his demise, as the person who shoots him does not recognise him in drag, and shoots him thinking he is a female intruder.

* ''WebAnimation/{{RWBY}}'': In Season 2, [[{{Adorkable}} Jaune]] talks with his teammate [[TheAce Pyrrha]] about the upcoming dance and is utterly stunned at the idea that an amazing girl like her wouldn't get a date[[note]]It's clear that she wants ''him'' to ask her, but [[ObliviousToLove he doesn't get it]] and [[IWantMyBelovedToBeHappy she's helping him try to ask Weiss]][[/note]], saying that if she doesn't, he'll wear a dress. When the dance rolls around, Pyrrha indeed shows up dateless, and Jaune (who came in a tux) leaves for a minute before returning in a white dress and asking her to dance. To his credit, he doesn't show any embarrassment at all and even ends up doing a dance routine with the rest of Team JNPR.

!!! Tropes about characters and their clothing choices:

Note that, since the 1960s or so in western culture, there tends to be little or no social stigma attached to women wearing "traditionally male" clothing. Once upon a time, however, a woman dressing like a man (e.g., wearing trousers) would be frowned upon, or even ''illegal'' in some jurisdictions.

* In ''VideoGame/TheLegendOfZeldaBreathOfTheWild'', Link has to crossdress in order to get into Gerudo Town, a town in which men are forbidden.

* In ''VideoGame/TheLegendOfZeldaBreathOfTheWild'', Link has to crossdress in order to get into Gerudo Town, a town in which men are forbidden.

* In ''VideoGame/LegendOfZeldaBreathOfTheWild'', Link has to crossdress in order to get into Gerudo Town, a town in which men are forbidden.

"Crossdresser" and "transvestite" aren't necessarily synonymous in RealLife. Many different (and often contradictory) definitions for each term can be found. This trope is intended to encompass ''all'' of them -- at least for purposes of troping. (It's also worth noting that the term "transvestite" is largely considered obsolete and pejorative nowadays.)

* ''Series/{{Mash}}'': Corporal Clinger, in attempt to prove that he is clinically insane and therefore unfit for active duty, regularly shows up in some form of women's dress, right down to the earrings and slip. Unfortunately, he can't pull off "crazy" because his personality is still the same.

* The whole shtick of ''Manga/ChottoEdoMade'' is about a girl who dresses like a boy and her love interest, a boy who dresses and acts like a girl (with [[TertiarySexualCharacteristics eyelashes to boot]]).

* The whole shtick of ''Manga/ChottoEdoMade'' is about a girl who dresses like a boy and her love interest, a boy who dresses and acts like a girl (with [[TertiarySexualCharacteristics eyelashes to boot]].

* ''WebAnumation/{{RWBY}}'': In Season 2, [[{{Adorkable}} Jaune]] talks with his teammate [[TheAce Pyrrha]] about the upcoming dance and is utterly stunned at the idea that an amazing girl like her wouldn't get a date[[note]]It's clear that she wants ''him'' to ask her, but [[ObliviousToLove he doesn't get it]] and [[IWantMyBelovedToBeHappy she's helping him try to ask Weiss]][[/note]], saying that if she doesn't, he'll wear a dress. When the dance rolls around, Pyrrha indeed shows up dateless, and Jaune (who came in a tux) leaves for a minute before returning in a white dress and asking her to dance. To his credit, he doesn't show any embarrassment at all and even ends up doing a dance routine with the rest of Team JNPR.

* ''WebAnumation/{{RWBY}}'': In one episode, as part of a self-imposed bet and in effort to make Pyrrha feel better, Jaune Arc lives up to his promise to wear a dress at the dance if she showed up minus a date.

[[Folder: Web Animation]]
''WebAnumation/{{RWBY}}'': In one episode, as part of a self-imposed bet and in effort to make Pyrrha feel better, Jaune Arc lives up to his promise to wear a dress at the dance if she showed up minus a date.