Crossdresser - Television Tropes & Idioms

And you thought James was the only one.

Sex roles in Japan are still quite rigidly defined compared to the United States. But just as Uncle Miltie found out in the 1950s, flouting them makes for good comedy. (And, occasionally, good drama.) Transvestites of both varieties can frequently be found in anime.

Much like in the west, the stereotypical crossdresser (okama) is usually suggested to be gay, although in some shojo series this is more to tease the audience than a 'negative' depiction.

For the usual western media depiction, see Transvestite.

See also Wholesome Crossdresser, Villainous Crossdresser, Bifauxnen, and Recursive Crossdressing. Not the same thing as Cross Dressing Voices. Absolutely not to be confused with transsexual and transgendered people, who are not crossdressers but have a gender identity that's either the opposite of their biological sex or non-normative.

Examples

Fay in Tsubasa Reservoir Chronicle sometimes does this. In the Alternate Universe Omake first Drama CD, he is shown wanting to join the girls as they dressed in maid outfits for the school festival, and in a strip comic for New Year's he wore a female kimono borrowed from Yuuko. He comments that he did it in secret because Kurogane hadn't let him wear the maid costume. Also, in the main storilyne, he wears what looks suspiciously like a wedding kimono during his stay in Nihon. Of course, said kimono had been provided by Tomoyo, so...
Poland in Axis Powers Hetalia crossdresses as a hobby.
Family Compo has so many Transsexuals and Crossdressers that it's hard to count. The main character's adoptive parents (both of them — that is, the "dad" is a woman, the "mom" is a man), his adoptive father's assistants (all transsexuals, some post-op, some not), several dozen bit characters, and one of the character's love interests — his adoptive sister — may or may not be a biological male, given that about every 6 months she'd switch genders as she was growing up ( It's never explained in the manga, and the end, the character realizes it doesn't really matter to him anyway.) Oh, and given how effeminate the main character is, he ends up in drag just about every other storyline. No, really, I'm not making this up!
Ukyo Kuonji and Tsubasa Kurenai from Ranma 1/2. (Also Konatsu in the manga.) Ukyou crossdresses less as the series goes on, though.
"Miss Aki" from Abenobashi Mahou Shoutengai was not very attractive at all.
Aoi from Youre Under Arrest certainly was.
Ryuunosuke from Urusei Yatsura is a girl, but was raised and dresses as a boy.
Oscar from Rose Of Versailles is another example of the girl-raised-as-a-boy plot device.
Makoto Mizuhara from El Hazard The Magnificent World, Yakumo from 3x3 Eyes and Yellow Belmont aka Lancer from Genesis Clumber Mospeada/Robotech Third Generation crossdress as a plot necessity rather than for their personal tastes. I.e.: Lancer crossdresses and poses as a female Idol Singer to act as a spy for the resistance group he's a part of.
All of the "princesses" in Princess Princess.
Kojiro (James) in Pokemon crossdresses as part of Team Rocket's various zany schemes, but also tends to crossdress seemingly for his own pleasure (as in the infamous "Beauty and the Beach" episode).
- Though he hasn't crossdressed at ALL in over four years...
- Ash Ketchum is also guilty of such activities, but he's only done it three times, only two of those being in an actual dress. Hell, the most recent incident has him shoved in a maid outfit... (see above image) Fetish Fuel, anyone?
  - To summarize: he's cross-dressed during each of the Pokégirls' (Misty, May, and Dawn) tenures with his travel party. The above image occured during Dawn's time in the group.
- To be fair to James, his partner Jesse crossdresses as a man just as often as he crossdresses as a girl.
The tenants, particularly Yuki, frequently dress up as women for various convoluted reasons in The Wallflower.
Fruits Basket contained a memorable scene in which Yuki crossdressed.
- Ayame, Momiji, and Ritsu all crossdress regularly. In the manga Akito is actually a woman pretending to be male.
The Slayers does this once a season, one episode per season. Fans of the series refer to this as Episode 17, as each crossdressing episode is the seventeenth episode in the given season. Ironically, not just the male cast, but often support characters introduced in the episode itself as well. Perhaps the most bizarre example is the "drag-on" sea dragon in the first season, who Gourry defeats by scratching its face and forcing the dandy dragon to retreat lest it gain any defacing scars.
Red Mage, the delusional Munchkin of 8-Bit Theater has a tendency to cross dress and pretend to be a woman named Deborah. He blames his father for this, but Thief states that he himself managed to put those memories into Red Mage's mind somehow.
- Obviously, he stole them into it.
Kazuki in Get Backers. The writers, especially in the anime, will take any excuse they can to get him into womens' clothing. Sometimes it's a misunderstanding, sometimes it's part of his job, sometimes it's favor for a friend... and then there's the official art of him in womens' swimsuits. The anime went so far as to lampshade it in the fourth ending: there are two points where the characters are divided by gender, and he's with the girls both times. To be fair, he's mistaken for a woman when he's not explicitly crossdressing.
G in From Eroica With Love.
Seki from Doki Doki School Hours likes to dress up in womens' attire - actually hoping he will impress girls that way.
Shinkan Poe, the grandson of the Big Bad Kublai in Uchuu Keiji Shaider, is a 5000-year old creature who drinks potions made of young girls to retain his/her beauty. In the last story arc however, in a Nightmare Fuel moment, Poe is revealed to have a hideous face without the potion, and to get the potion made again, captures Shaider's female partner Annie.
Hourou Musuko has this as a large part of its plot, as a feminine boy, Shuichi, and a tomboyish girl, Yoshino, begin frequently dressing in girl's and boy's clothing respectively, much preferring and wishing to be the other gender. They also befriend a transsexual named Yuki, who acts as a Cool Big "Sis" to them.
Many operas were originally composed on the assumption that at least one castrato would be in the cast. There are several male roles in opera (list available on that other wiki) that were originally written for castrati, but currently sung by females.
Mr. 2 Bon Clay from One Piece. Oh my goodness. His fighting style is even called "Okama Kenpo", and he has no female partner in Baroque Works because "he counts as a man and a woman".
Ouran High School Host Club has a lot of crossdressing.
Gintama has the Okama bar that created the lovely Paako and Zurako. Gintoki, Shinpachi and even Kagura have no problems crossdressing when they need to...or just for the hell of it, actually. And there's also Yagyuu Kyuubei.
Eyeshield21 had Ootawara and Sakuraba dressed as maids (during a public practice) as a punishment for losing a trivia game during a school festival. This, however, only increased Sakuraba's popularity. Hiruma also dressed like a maid to spy on the players from the American team. Panther got a good laugh out of it.
In Kuroshitsuji, Ciel has to crossdress quite a few times for the sake of investigating. One instance involved him dressing in a fancy, flowery and pretty dress (looking astonishingly good in it) and going to a ball. Unfortunately for him, his fiancee Elizabeth was there too, and it takes a lot of effort for him and Sebastian to avoid her.
In the Black Cat anime, both Train and Sven are shown crossdressing. For Sven, he wears a very frilly, fancy dress to try to lure a killer for a bounty. It doesn't work. For Train, after transforming into a child, while Eve and Kyoko go out to buy clothes the right size for him, he's forced to wear Eve's dress.
Negi in Mahou Sensei Negima got this once, being forced to dress as a fox-girl (Fan Nickname: Kitsunegi). The silly cuteness was meant to attract customers to the class' haunted house. Yeah.
- It worked like a charm.
Neon Genesis Evangelion's main character Shinji Ikari has crossdressed on two occasions, once wearing Asuka's spare plugsuit (complete with breast plates) and again when he and Asuka are training to defeat Israfel they wear identical ... "jazzercise" outfits.
How in hell's name did we actually make it this far without mentioning the scene in The Genderbending of Haruhi Suzumiya where Haruki has Mitsuru wear a maid outfit for a photo shoot?!
Lelouch does this at least twice in the picture dramas of Code Geass. In one of them, the Student Council has a crossdressing festival so everyone crossdresses (and Suzaku... mentions having done it a few times before?).
- Kanon is a crossdresser. He was persecuted for it until he met Schneizel.
How have we managed not to mention the Creepy Twins Hansel and Gretel in Black Lagoon? They switch clothes, voices and weapons and we never know what their born genders are.