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"
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 Drag Queen, 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 Real Life. 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... even though it's derived from literally just the words for "cross dresser" in Latin.)
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:
- Wholesome Crossdresser: Crossdressing characters (of either sex) presented in a positive (or at least neutral) way. Often presented as physically attractive.
- Creepy Crossdresser: Crossdressing characters (nearly always men) played for weirdness, creepiness, Squick value, or to show that a character is evil or deranged.
Tropes about dressing as disguise:
- Disguised in Drag: Men disguise themselves as women.
- Sweet Polly Oliver: Women disguise themselves as men. See Samus Is a Girl for the reveal.
- Recursive Crossdressing: Women disguise themselves as men disguised as women, vice versa, or any permutations thereof.
Tropes about other character's responses:
- Dragged into Drag: Girls love helping boys dress as girls.
- Sweet on Polly Oliver: Straight guys find another guy disturbingly attractive... because "he" is actually a girl.
- Attractive Bent-Gender: Men dressing as (or transformed into) women become hot women.
- Unsettling Gender Reveal: The confusion caused by the person a character was crushing on turning out to be the opposite gender of what they assumed.
- Ryou and Osamu from Bokura no Hentai don't fit either Wholesome Crossdresser or Creepy Crossdresser completely. While originally The Bully 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 Wholesome Crossdresser early on but quickly goes down a slippery slope of unsettling behavior and depression.
- Boss from 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 High School Ninja Girl, Otonashi-san 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.
- Nozomu Nozomi is about a late-blooming middle school student who discovers he likes to wear girl's clothing when he's Dragged into Drag to redeem a bet and later suffers an inexplicable Gender Bender 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 Wholesome Crossdresser into a Sweet Polly Oliver under the influence of female puberty, nodding at Attractive Bent-Gender. Recursive Crossdressing and Sweet on Polly Oliver 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 Gender Bender who 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 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. This characteristic died down as the series progressed.
- Shiratori from The High School Life of a Fudanshi likes to dress in women's clothing.
- City Hunter: 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 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.
- 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.
- A sketch song of the German comedy group "Die Insterburgs" collects mishaps in a sex shop. One guy buys a sex education book. Somehow he manages to misunderstand everything and at the end of the song, he'll go buy a skirt.
- Male example: In Gankona, Unnachgiebig, Unità, Italy crossdressed as Sailor Moon. Let's just say it left very little to the imagination.
- Khaos Omega 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 Fairytale Wedding Dress), Jace Davies (a transformation-induced Chaos Reaction near his own Anise), and Jayden Omega (a sixth birthday present) also obtain.
- 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.
- Nevada: One of the characters in the book is convinced he's just this and not a trans woman.
- 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.
- Monty Python's Flying Circus 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.
- The Benny Hill Show did it regularly.
- A Bit of Fry and Laurie did this all the time, too.
- Dick & Dom in da Bungalow, including Mr Richard McCourt dancing the tango in a very fetching dress.
- Parodied on Little Britain, which featured Emily and Florence, who would dress and attempt to act like 19th century women and insisted that they were lay-dees. Florence has a moustache.
- Coronation Street, of all programmes, had a particularly bizarre plot-line involving Audrey Roberts and a transvestite boyfriend....
- In Princess Returning Pearl Xiao Yan Zi and Zi Wei sometimes dress as male when going outside. No one is fooled.
- Night and Day'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 womens clothes and goes by the name of Beverly.
- Father Brown: The Victim of the Week in "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.
- Mash: Corporal Klinger, 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.
- Valkyria Chronicles 4: Handled in a refreshingly tasteful manner for a Japanese game. The specific details of Rosetta's gender and sexuality are not clear, but it is clear that she considers her feminine attire to be cross dressing. This is not played for laughs or even mentioned at all - nobody in Squad E seems to care one way or another.
- In The Legend of Zelda: Breath of the Wild, Link has to crossdress in order to get into Gerudo Town, a town in which men are forbidden.
- Averted with Tedd in El Goonish Shive; he may own more skirts than his girlfriend, but he doesn't wear them as a boy.
- Lady Fiona Fiziwigg of the mystery/adventure webcomic The Continentals cross dresses and lives her life as a man. Read it here.
- Sock from Welcome to Hell wears a Skirt over Slacks. This doesn't get mentioned in-series. On one hand, Socks is a demon in hell whose job is to make people Driven to Suicide. On the other hand, he completely sucks at his job and seems more like a plucky keet than a villain.
- RWBY: In Season 2, Jaune talks with his teammate Pyrrha about the upcoming dance and is utterly stunned at the idea that an amazing girl like her wouldn't get a datenote , 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.
- Chef from Total Drama often wears dresses or female uniforms during his various roles in the Show Within a Show.
- Never shown but there are a few jokes in The Weekenders that imply Carter crossdresses.
- King of the Hill 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 Kaeloo admits once under the effects of Truth Serum that he enjoys dressing up as a girl when he is alone. In several games the characters are playing, he is Dragged into Drag, but in some episodes he does it on his own. This has led to some... awkward moments on the show◊.