History Main / WholesomeCrossdresser

* Like her VideoGame [[{{Persona 4}} counterpart]] [[spoiler: Naoto Shirogane]] of ''[[Anime/{{Persona 4}} Persona 4: The Animation]]'' is one of these. [[ItWasHisSled You should know this already.]]

* ''{{Persona 4}}'' [[spoiler:Naoto is a reverse trap.]] [[ItWasHisSled You should know this by now.]]

* Like her VideoGame [[{{Persona 4}} counterpart]] [[spoiler: Naoto Shirogane]] of ''[[Anime/{{Persona 4}} Persona 4: The Animation]]'' is one of these.

* ''{{Persona 4}}'' [[spoiler:Naoto is a reverse trap.]]

* Salome "Sam" Fredericks in TadWilliams' ''Literature/{{Otherland}}'' series pretends to be a boy online, complete with [[TomboyishName Tomboyish Nickname]], to avoid getting singled out for her gender. This causes complications when her friend, [[LittlestCancerPatient Orlando Gardiner]], seeks her out in RealLife.

* Salome "Sam" Fredericks in TadWilliams' ''{{Otherland}}'' series pretends to be a boy online, complete with [[TomboyishName Tomboyish Nickname]], to avoid getting singled out for her gender. This causes complications when her friend, [[LittlestCancerPatient Orlando Gardiner]], seeks her out in RealLife.

* Jack Donaghy of ''[[Series/ThirtyRock 30 Rock]]'' reveals that he exclusively wore hand me downs until he was 12. His older siblings were all girls.[[hottip:* :"Apollo, Apollo": Season 3, Episode 16]]

* One of the "edgy" things about Baz Luhrmann's modern remake of ''Theatre/RomeoAndJuliet'' is having Mercutio (plaued by [[Series/{{Lost}} Harold]] [[Film/TheMatrix Perrineau]]) show up to the Capulets' ball - imagined in the remake as a Halloween party -- dressed in drag. He stays in drag for a lot longer than is really necessary. Then again, it's [[AmbiguouslyGay Mercutio.]]

* In ''VideoGame/AnimalCrossing'', you can wear any clothing or accessory items, even those that are obviously intended for the opposite sex. This extends in subsequent games to even unlocking the ability to have girl's hairstyles or shoes on a boy or vice versa. The only thing you can't do is change the face style or actually use the opposite sex clothes model (that is, putting a dress on a boy character will make it still look like a shirt, and putting a shirt on a girl will still look like a dress)- though, this last restriction is removed in the 3DS version, which has skirts, pants, and dresses as separate kinds of items.
** Blanca, the cat with the blank face, is evidently a male, even though "Blanca" is the feminine form, the gibber-clip is the highest-pitched one used for females, and the outfit is the female skirt. So, uh....there you go.
*** She has no name in Japan, and internationally she's been changed into a girl. Bob, another cat, is still a boy though purple and he wears a long pink floral "shirt".
** Also, Gracie is a guy in the Japanese versions.

*** She has no name in Japan, and internationally she's been changed into a girl. Bob, another cat, is still a boy though and he wears a long floral "shirt".

* ''{{Theatrica}}'' with the character Vivian.

* Dana and other Elle-Boys in the ''Webcomic/JetDream'' RemixComic always dress as females, but are fairly chaste and strictly heterosexual, apparently due to the (fictional) publisher's misguided attempt to pass the ComicsCode and/or [[AuthorAppeal Publisher Appeal]].

*** Then, the V-Cinema DVD Special took this to ridiculously funny levels, when in a bizarre (long story) moment, Kotoha and Mako dress and act like school boys... and then Ryuunosuke, Chiaki and Genta reveal that they're cross-dressers as well. The biggest WTF moment was when Takeru, who's calmly sitting... suddenly flips his clothes and reveal himself to be a rather CONVINCING cross dresser too. [[CrowningMomentOfFunny What. The. Hell.]]

** In the POVSequel, Timon was still wearing the outfit when he reunites with his Ma and Uncle Max, and [[CrowningMomentOfFunny they don't comment on it until after Timon has left the scene]].

* WoodyWoodpecker has done this time to time, the most memorable instances being ''Chew-Chew Baby'', ''Drooler's Delight'' and ''The Woody Woodpecker Polka.''
* Pleakley in ''LiloAndStitch'' and ''LiloAndStitchTheSeries''.

* Part of Override's bio from her toy on ''TransformersCybertron'' (only available after entering her Cyber Key code on the TFC website) states that in order to win leadership of Speed Planet she entered the race disguised as a male. Exactly how this works (or for that matter why she'd do it) isn't mentioned.

* Examples from ''TheFairlyOddparents'':

** In part 3 of ''Wishology'', Timmy's dad has been known to wear a dress with a blonde wig. [[spoiler:However, this was AllJustADream in the Darkness' LotusEaterMachine.]]

* [[TinyToonAdventures Buster Bunny]], usually for the same reason as [[WesternAnimation/LooneyTunes Bugs]], to trick people.
* On ''{{Jimmy Two-Shoes}}'', both Jimmy and Lucius do this while being flight attendents.

* Both Fred and Barney of ''TheFlintstones'' do this oddly often. Barney does it VERY often in the Fruity Pebbles ads, presumably just to get Fred's Pebbles.
* AmbiguouslyGay King Julien of ''WesternAnimation/{{Madagascar}}'' and ''ThePenguinsOfMadagascar'' has worn skirts occasionally, though this may not count as he's a lemur and doesn't normally wear anything at all.

* ''TheAmazingChanAndTheChanClan'' character Stanley Chan has crossdressed on more than one occasion, twice for disguises and one for the sake of [[RuleOfFunny being hilarious]]. He pulls it off quite well, too.
* The ''ChristmasEpisode'' of ''KidsNextDoor'' opens with the [[HiveMind Delightful Children]] impersonating the Kids Next Door. The Delightful Children include one brown-skinned boy and a chubby girl, they are presumably the ones that dressed as Numbuh 5 and Numbuh 2, respectively.

* Several minor examples from ''TheSimpsons'':

* ''AllGrownUp'' has Phil dressed as his twin sister Lil. He seems to develop a crush on [[HoYay another boy]].
* WesternAnimation/SheZow is a LegacyHero superheroine whose powers-enhanced costume are granted to whoever wears her ring. Originally meant for females in the family line, the lastest member in the family line who wears the ring is [[PunnyName Guy Hamdon]], a pre-teenage boy. As a result, he wears [=SheZow=]'s female-intended costume as he fights crime. Guy seems to be completely indifferent to this, although he didn't take it too well at first.

* Ayumu Mikoshiba from ''Manga/OsatukeMikoMikoChan'' is one, however reluctantly. [[spoiler:Rei]] however, has no qualms about [[spoiler:his]] cross-dressing.

*** Except male Kirlia's can still become Gardevoirs if it just evolves normally.

* ''Disney/{{Mulan}}'':
** Subverted. Mulan's three friends make "Concubines." "''Ugly'' Concubines."
** Although Mulan obviously is one.

** A [[MemeticMutation common]] ImageMacro used for {{trolling}} shows a picture of him and says "[[EvenTheGuysWantHim Everyone's gay for Bridget]]". Very confusing if you haven't played the game. There's a reason UnsettlingGenderReveal used to be called "Dropped A Bridget On Him".

* Danny the Street, in Creator/GrantMorrison's ''Comicbook/DoomPatrol'', is a transvestite sentient street.

* Par for the course in any story on {{Literotica}} that's in the Transsexuals/Crossdressers section and doesn't contain either [[GenderBender magic]] or [[BondageIsBad bondage]].

* Makoto/"Mako-chan" in ''{{Minami-ke}}''. [[ClarkKenting All it seems to take]] is a hair clip and a skirt and bam! Uncannily cute & convincing girl. Like, "make you doubt your own preference" convincing. Interestingly, his first comment in the second season is being glad he can dress normally again... and GilliganCut to him in a girl's outfit, with the comment the [[NoFourthWall girls can't accept him otherwise]].
** You missed the part where Kana took one look at Normal!Makoto and ''shut the door in his face''.