History Main / Crossdresser

''Series/{{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.

* ''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.

* 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 ''Zettai Ryouiki''. 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.

* 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), Jace Davies (a transformation-induced Chaos Reaction near his own Anise), and Jayden Omega (a sixth birthday present) also obtain.

[[folder: Literature]]
* ''Literature/{{Nevada}}'': One of the characters in the book is convinced he's just this and not a trans woman.

* Sock from ''Webcomic/WelcomeToHell'' wears SlacksOverSkirt. This doesn't get mentioned in-series. On one hand, Socks is a demon in hell whose job is to make people DrivenToSuicide. On the other hand, he [[MinionWithAnFInEvil completely sucks at his job]] and seems more like a plucky {{keet}} than a villain.

* Boss from ''{{Anime/Hamtaro}}'' (yes, that's right, HAMTARO) does this occasionally in the Japanese series. Originally he only did it when acting as the "nurse chief" of the Ham-Ham Nurse Team (though none of the other boys were part of it, so it's unknown why Bijou wouldn't have been the nurse chief), but later on he seems more than eager to cross-dress for other reasons, including: pretending to be a girl to attract Flora's presumed husband so she wouldn't have to marry him (it turned out that the male monkey Pepe was to marry a female monkey, and Flora wasn't getting married, but still), dressing like a girl for Sparkle's show, and dressing as a female ninja in the final Nin-Ham episode (complete with makeup, which is strange since he always dressed as a male ninja previously).

* Stumpy from ''WesternAnimation/{{Kaeloo}}'' admits once [[spoiler: under the effects of TruthSerum]] that he enjoys dressing up as a girl when he is alone. In several games the characters are playing, he is DraggedIntoDrag, but in some episodes he does it on his own. This has led to some... [[http://kaeloo.wikia.com/wiki/File:Stumpypoledancing.gif awkward moments on the show]].

* Sparkes Lukanta of ''[[http://www.thewretchedoneswebcomic.com The Wretched Ones]]'' cross dresses as a female on a daily basis.

* Jessie and James, members of Team Rocket from ''{{Anime/Pokémon}}'' were shown to cross dress frequently whenever they go in disguise with Jessie sometimes dressing up as a man and James dressing up as a woman. James in particular has cross dressed way more than Jessie has as he dressed himself up as a schoolgirl, a ballerina, and even went as far as buying fake breasts and entering into a beauty pageant with them, which caused an episode of the series to get banned because of him. He did most of the cross dressing in the original series but has not done it frequently.

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 self-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.

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 {{Transsexual}}, which describes people who self-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 transsexual.

** Parodied on ''LittleBritain'', which featured Emily and Florence, who would dress and attempt to act [[BornInTheWrongCentury like 19th century women]] and insisted that they were ''lay-dees''. Florence has a moustache.

* Boss from ''Anime/Hamtaro'' (yes, that's right, HAMTARO) does this occasionally in the Japanese series. Originally he only did it when acting as the "nurse chief" of the Ham-Ham Nurse Team (though none of the other boys were part of it, so it's unknown why Bijou wouldn't have been the nurse chief), but later on he seems more than eager to cross-dress for other reasons, including: pretending to be a girl to attract Flora's presumed husband so she wouldn't have to marry him (it turned out that the male monkey Pepe was to marry a female monkey, and Flora wasn't getting married, but still), dressing like a girl for Sparkle's show, and dressing as a female ninja in the final Nin-Ham episode (complete with makeup, which is strange since he always dressed as a male ninja previously).

* Jessie and James, members of Team Rocket from ''Anime/Pokémon'' were shown to cross dress frequently whenever they go in disguise with Jessie sometimes dressing up as a man and James dressing up as a woman. James in particular has cross dressed way more than Jessie has as he dressed himself up as a schoolgirl, a ballerina, and even went as far as buying fake breasts and entering into a beauty pageant with them, which caused an episode of the series to get banned because of him. He did most of the cross dressing in the original series but has not done it frequently.

* Jessie and James, members of Team Rocket from ''Anime/{{Pokémon}}'' were shown to cross dress frequently whenever they go in disguise with Jessie sometimes dressing up as a man and James dressing up as a woman. James in particular has cross dressed way more than Jessie has as he dressed himself up as a schoolgirl, a ballerina, and even went as far as buying fake breasts and entering into a beauty pageant with them, which caused an episode of the series to get banned because of him. He did most of the cross dressing in the original series but has not done it frequently.

* Jessie and James, members of Team Rocket from ''Anime/Pokemon'' were shown to cross dress frequently whenever they go in disguise with Jessie sometimes dressing up as a man and James dressing up as a woman. James in particular has cross dressed way more than Jessie has as he dressed himself up as a schoolgirl, a ballerina, and even went as far as buying fake breasts and entering into a beauty pageant with them, which caused an episode of the series to get banned because of him. He did most of the cross dressing in the original series but has not done it frequently.

The following are subtropes of {{Crossdresser}}:

* CoronationStreet , of all programmes, had a particularly bizarre plot-line involving Audrey Roberts and a transvestite boyfriend....

"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.

* ''Manga/NozomuNozomi'' is about a late-blooming middle school student who discovers he likes to wear girl's clothing when he's DraggedIntoDrag to redeem a bet and later suffers an inexplicable GenderBender when he's nearly caught wearing his sister's clothes. Over the next year he experiences virtually every other crossdressing trope as he gradually morphs from a WholesomeCrossdresser into a SweetPollyOliver under the influence of [[TheMindIsAPlaythingOfTheBody female puberty]], nodding at or hanging a lampshade on AttractiveBentGender. RecursiveCrossdressing and SweetOnPollyOliver along the way until he's no longer sure if he's a boy who likes to dress as a girl or a girl who is forced to dress as a boy. This makes him a rare example of a GenderBender character who [[ThirdLawOfGenderBending actually wants to dress as her new sex]] but is prevented by their circumstances.

'Cuz I wanted to be dressed just the same"''