[[Anime/{{Pokemon}} http://tvtropes.org/pmwiki/pub/images/Ashcrossdressesagain.png]]
[[caption-width:320:Even worse, he's done this not once, but ''twice'' before.]]

Sex roles in Japan are still quite rigidly defined compared to the United States. But just as [[TheMiltonBerleShow 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 [[FanService tease the audience]] than a 'negative' depiction.

For the usual western media depiction, see {{Transvestite}}.

See also WholesomeCrossdresser, VillainousCrossdresser, {{Bifauxnen}}, and RecursiveCrossdressing. Not the same thing as CrossDressingVoices. Absolutely not to be confused with [[{{Transsexual}} 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 ''TsubasaReservoirChronicle'' sometimes does this. In the AlternateUniverse 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 [[XxXHolic 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 [[YaoiFangirl Tomoyo]], [[SoYeah so...]]
* Poland in ''AxisPowersHetalia'' crossdresses as a hobby.
* ''{{Family Compo}}'' has so many {{Transsexual}}s and {{Crossdresser}}s 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 [[WillTheyOrWontThey 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 ([[spoiler: 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. [[http://www.onemanga.com/Family_Compo/ No, really]], I'm not making this up!
* Ukyo Kuonji and Tsubasa Kurenai from ''[[RanmaOneHalf Ranma 1/2]]''. (Also Konatsu in the manga.) Ukyou crossdresses less as the series goes on, though.
* "Miss Aki" from ''AbenobashiMahouShoutengai'' was not very attractive at all.
* Aoi from ''YoureUnderArrest'' certainly was.
* Ryuunosuke from ''UruseiYatsura'' is a girl, but was raised and dresses as a boy.
* Oscar from ''RoseOfVersailles'' is another example of the girl-raised-as-a-boy plot device.
* Makoto Mizuhara from ''ElHazardTheMagnificentWorld'', Yakumo from ''[[ThreeByThreeEyes 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 IdolSinger to act as a spy for [[LaResistance the resistance group]] he's a part of.
* All of the "princesses" in ''PrincessPrincess''.
* Kojiro (James) in ''{{Pokemon}}'' crossdresses as part of Team Rocket's various {{zany scheme}}s, 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...
*** [[spoiler:In DP 146, James dresses as Jessie's Contest alterego when she falls ill. And he WINS.]]
** 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?
*** The first incident Ash resorted to crossdressing, he was locked out of the Celadon Gym due to insulting the perfume and had to change his appearance to get inside. Jessie and James were on hand to get him an outfit, but it couldn't hope to last.
*** To summarize: he's cross-dressed during each of the [[TheSmurfettePrinciple 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.
** Pokemon also tend to crossdress, such as Dawn's male Piplup wearing a [[RealMenWearPink pink]] female cheerleader uniform. However, they ''are'' Pokemon..
* The tenants, particularly Yuki, frequently dress up as women for various convoluted reasons in ''TheWallflower''.
* ''FruitsBasket'' contained a memorable scene in which Yuki crossdressed.
** Ayame, Momiji, and Ritsu all crossdress regularly. In the manga [[spoiler:Akito is actually a woman pretending to be male]].
* TheSlayers does this once a season, one episode per season (except seasons 4-5). 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 [[EightBitTheater 8-Bit Theater]] has a tendency to cross dress and pretend to be a woman named Deborah. He [[FreudianExcuse blames his father]] for this, but Thief states that he himself managed to put those memories into Red Mage's mind somehow.
** Obviously, he [[IncrediblyLamePun stole them into it]].
* Kazuki in ''GetBackers''. 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 [[LampshadeHanging 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 FromEroicaWithLove.
* Seki from ''DokiDokiSchoolHours'' 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 [[spoiler:to have a hideous face without the potion, and to get the potion made again, captures Shaider's female partner Annie]].
* ''HourouMusuko'' 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 [[CoolBigSis Cool Big Sis]] to them.
* Many operas were originally composed on the assumption that at least one [[http://en.wikipedia.org/wiki/Castrato castrato]] would be in the cast. There are several male roles in opera (list available on [[http://en.wikipedia.org/wiki/Breeches_role#Opera that other wiki]]) that were originally written for castrati, but currently sung by females.
* Mr. 2 Bon Clay from ''OnePiece''. 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".
* ''OuranHighSchoolHostClub'' [[{{Understatement}} 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 [[spoiler: 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 [[DancesAndBalls ball]]. Unfortunately for him, his [[ArrangedMarriage fiancee Elizabeth]] was there too, and it takes a lot of effort for him and Sebastian to avoid her.
** Actually, Ciel has only ever crossdressed once within the series for the aforementioned ball. The frills and ribbons were common on men's clothes in that [[VictorianLondon era]]. There was an official manga splashpage of Ciel in a dress, but it wasn't something he ever wore in the series.
*** The mangaka has some sketches of Ciel in an editted version of an Alice in Wonderland outfit with bloomers instead of an actual dress (which can be found [[http://d-6th.com/blog/2009/05/index_3.php here]]) on her blog. Not sure if it's really crossdressing, but it's worth mentioning.
* In the ''BlackCat'' 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 ''MahouSenseiNegima'' got this once, being forced to dress as a fox-girl (FanNickname: Kitsunegi). [[AttractiveBentGender The silly cuteness was meant to attract customers]] to the class' haunted house. [[SoYeah Yeah]].
** It worked like a charm.
* ''NeonGenesisEvangelion'''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.
* At one point in the third chapter of ''[[FanFic/SuzumiyaHaruhiNoSeitenkan The Melancholy of Haruki Suzumiya]]'', Haruki has Mitsuru wear a maid outfit for a photo shoot.
* [[MagnificentBastard Lelouch]] does this at least twice in the picture dramas of CodeGeass. 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 [[AllThereInTheManual is a crossdresser.]] He [[TruthInTelevision was persecuted for it]] until he met Schneizel.
* The CreepyTwins Hansel and Gretel in BlackLagoon. They switch clothes, voices and weapons and we never know what their born genders are.
* Yozak from ''KyoKaraMaoh'' is a 'spy' who crossdresses on a regular basis, to the point where he now carries a dress around just to have one handy. Which is quite hilarious, seeing as he's ripped and rather manly.
* Ryo Hayama of ''Bremen'' fully dresses up as a girl which includes wigs, fake boobs, platform shoes, [[FemmeFatalons fake nails]], etc. [[BerserkButton Just beware about calling him one]].
----
<<|AnimeCharacterTypes|>>
<<|TransgenderTropes|>>
<<|TurnOnTropes|>>