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[[caption-width-right:350:Music/DavidBowie as Creator/TildaSwinton as Music/DavidBowie]]
->''"Whatever happened to Fay Wray?\\
That delicate satin-draped frame\\
As it clung to her thigh\\
How I started to cry\\
'Cause I wanted to be dressed just the same"''
-->-- '''Dr. Frank N. Furter''', ''Film/TheRockyHorrorPictureShow''

In short, this trope is about "dressing in the clothing of the opposite sex." The long version can get a little more complicated.

Crossdressers may be men dressing as women, or women dressing as men. Contrary to popular belief, crossdressing does not necessarily imply homosexuality. An element of sexual arousal ("transvestic fetishism") may be involved in dressing, but not necessarily. And sometimes the primary purpose for crossdressing is simply disguise. This supertrope covers all the various possibilities and permutations.

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.

"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.)

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.

The following are subtropes of Crossdresser:
!!! Tropes about characters and their clothing choices:
* WholesomeCrossdresser: Crossdressing characters (of either sex) presented in a positive (or at least neutral) way. Often presented as [[AttractiveBentGender physically attractive]].
* CreepyCrossdresser: Crossdressing characters (nearly always men) played for weirdness, creepiness, {{Squick}} value, or to show that a character is evil or deranged.
%% * MenInDressesAreFunny: Crossdressing men played primarily for humor.

!!! Tropes about dressing as disguise:
* DisguisedInDrag: Men disguise themselves as women.
* SweetPollyOliver: Women disguise themselves as men. See SamusIsAGirl for the reveal.
* RecursiveCrossdressing: Women disguise themselves as men disguised as women, vice versa, or any permutations thereof.

!!! Tropes about other character's responses:
* DraggedIntoDrag: Girls love helping boys dress as girls.
* SweetOnPollyOliver: Straight guys find another guy disturbingly attractive... because "he" is actually a girl.
* AttractiveBentGender: Men dressing as (or [[GenderBender transformed into]]) women become ''hot'' women.
* UnsettlingGenderReveal: The confusion caused by the person a character was crushing on turning out to be the opposite gender of what they assumed.

See Also AmbiguousGender, ViewerGenderConfusion, {{Bifauxnen}}, and DudeLooksLikeALady, tropes which share some common aspects with the above but generally are not about deliberate crossdressing. Similarly, UnplannedCrossdressing technically involves crossdressing, but it's unintentional on the character's part. Like DragQueen, CrosscastRole involves crossdressing, but only in the context of "performance" -- here, an actor playing a part.
%% Ideally, this trope should not have any examples -- all should fall under one of the various subtropes listed. Remaining examples are mostly because it's unclear from context whether they should go under WholesomeCrossdresser or CreepyCrossdresser.


[[folder: Anime & Manga]]
* Ryou and Osamu from ''Manga/BokuraNoHentai'' don't fit either WholesomeCrossdresser or CreepyCrossdresser completely. While originally TheBully and disgusted at the other protagonists, Ryousuke is presented quite sympathetically due to his back story and poor home life. Osamu is presented as something of a WholesomeCrossdresser early on but quickly goes down a slippery slope of unsettling behavior and depression.
* 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).
* 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/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 or hangs a lampshade on virtually every other crossdressing subtrope as he gradually morphs from a WholesomeCrossdresser into a SweetPollyOliver under the influence of [[TheMindIsAPlaythingOfTheBody female puberty]], nodding at AttractiveBentGender. RecursiveCrossdressing and SweetOnPollyOliver along the way until he no longer knows 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 an involuntary GenderBender who [[ThirdLawOfGenderBending actually wants to dress as their new sex]] but is prevented by their circumstances, with the added irony that for much of the year he's only crossdressing when everyone thinks he isn't.
* 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. This characteristic died down as the series progressed.
* Shiratori from ''Manga/TheHighSchoolLifeOfAFudanshi'' likes to dress in women's clothing.
* ''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.
** In the third game of the Galaxy Angel II trilogy this nearly happens to Kazuya again (again in Natsume's route, here affecting Kazuya whereas the tomboyish Anise is the one affected in her route), but Lily quickly neutralizes the cause to protect Kazuya's so-called secret.

[[folder: Fan Works]]
* 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.

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

[[folder: Live Action TV]]
* British television has a proud tradition of men dressing as women for comedy. It probably goes back to how men (or boys) played female roles in Shakespeare's day; re-enforced by their tradition of single-sex schools (few plays have all-male or all-female casts, so if a single-sex school has a drama program AT ALL, SOMEBODY will get cross-cast.) Some have gone so far as to say that there is nothing funnier to a British audience than a man dressed up like a woman.
** ''Series/MontyPythonsFlyingCircus'' did this in every episode. It probably helped that the troupe didn't usually have any women anyway (apart from Carol Cleveland), so at least some of the crossdressing was actually pretty necessary.
** ''Series/TheBennyHillShow'' did it regularly.
** ''Series/ABitOfFryAndLaurie'' did this all the time, too.
** ''Series/DickAndDomInDaBungalow'', including Mr Richard [=McCourt=] dancing the tango in a [[http://www.youtube.com/watch?v=06szyd9ccOQ&t=5m50s very fetching dress]].
** Parodied on ''Series/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.
* ''Series/CoronationStreet'', of all programmes, had a particularly bizarre plot-line involving Audrey Roberts and a transvestite boyfriend....
* In ''Series/PrincessReturningPearl'' Xiao Yan Zi and Zi Wei sometimes dress as male when going outside. No one is fooled.
* ''Series/NightAndDay'''s Fiona Brake and Dennis Doyle both have forays into cross-dressing; Fiona in a bid to seduce her gay husband, and Dennis because he briefly thinks he might be intersex. Also, in in the final episode, set four years into the future, we learn that Ryan Harper now wears women’s clothes and goes by the name of Beverly.
* ''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.
* ''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.

[[folder: Web Comics]]
* {{Averted}} with Tedd in ''Webcomic/ElGoonishShive''; he may own more skirts than his girlfriend, but he [[GenderBender doesn't wear them as a boy.]]
* Lady Fiona Fiziwigg of the mystery/adventure webcomic ''Webcomic/TheContinentals'' cross dresses and lives her life as a man. Read it [[http://www.theduckwebcomics.com/The_Continentals here.]]
* Sock from ''Webcomic/WelcomeToHell'' wears a SkirtOverSlacks. 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.

[[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.

[[folder: Western Animation]]
* Chef from ''WesternAnimation/TotalDrama'' often wears dresses or female uniforms during his various roles in the ShowWithinAShow.
* Never shown but there are a few jokes in ''WesternAnimation/TheWeekenders'' that imply Carter crossdresses.
* ''WesternAnimation/KingOfTheHill'' episode "The Peggy Horror Picture Show" has Peggy befriending a woman named Caroline who makes her feel better about being less than perfectly feminine. However, she turns out to be a crossdresser and Peggy's self-esteem drops even lower than before when she finds out. By the end of the episode, Caroline mends fences by explaining that people like her admire women like Peggy who are strong, confident, and not afraid to be themselves.
* 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]].