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Yes, that is a guy, and no, those breasts are not real. (It's a trap!)Mirror image, see no damage, see no evil at all
Cupie dolls and urine stalls will be laughed at
The way you're laughed at now.
Lady, maybe, or Host? I find I really don't mind.
The polar opposite of the Villainous Crossdresser, the Wholesome Crossdresser is usually well-groomed, compassionate, nice and above all, so convincing that his or her sex is mentioned on occasion just to remind newer viewers. Sometimes the traits aren't flamboyant as much as so very stereotypical compared to the rest of the cast you can make a decent guess. There's a fair chance someone will get a crush on them, although this is usually resolved after The Reveal.
Interestingly, the specific source of contention doesn't occur outside the series. Merchandise and other fan stuff will treat the character as 'genuine' or at least a strange equal-opportunity, especially if the apparent gender is female, and even if the character is only disguising themselves for plot reasons. There's also a good chance that even if this reason is resolved later, the character will usually still keep dressing the same way.
This is easier to do than it sounds, especially if most of your characters look alike anyway. If your artists also like costumes, the Wholesome Crossdresser is the prime target since you don't have to show the relevant bits. This becomes an easy way to simply tell us that the character crossdresses without ever depicting said character au naturel. Sometimes though, artists become lazy with this and draw characters with actual flesh in the wrong places, especially if a character is Hiding In The Harem.
One slightly controversial element is that most non-plot-related crossdressers tend to fufill the standard stereotypes, though often in a positively intended way.
In a reference to one Admiral Ackbar's line in Star Wars, The Internet usually refer to these overly effeminate guys as "traps". Their female counterparts are commonly known as "Reverse Traps".
See also Attractive Bent Gender, Sweet Polly Oliver. Contrast Sweet On Polly Oliver.
Examples:
Anime and Manga
Comic Books
- We must not forget Quality Comics's Madame Fatal, the first cross-dressing superhero. "She" was really Richard Stanton, retired actor, who took up the up the persona of a harmless-seeming old lady after his daughter was kidnapped. Because no-one suspects the old lady.
- And then there's the Goddamn Maidman!
Film
- All three protagonists of The Adventures Of Priscilla Queen Of The Desert, to varying degrees. Terrence Stamp plays a hard-drinking but patient transsexual, Guy Pearce a bitchy, high-strung Performance Artist, and Hugo Weaving is the timid, sweet-natured drag queen who persuades them to do a cabaret act in the middle of the desert. That breaking sound you heard was your brain.
- To Wong Fu, Thanks For Everything, Julie Newmar. John Leguizamo, Patrick Swayze, and Wesley Snipes all as crossdressing drag queens. Vida and Noxeema even convince Chi-Chi to give up the boy she has a crush on to the girl in town that likes him, as it wouldn't be fair to him.
- Some Like It Hot.
- In Takashi Kitano's Zatoichi Geisha Seitaro 'Osei' Naruto is actualy a man.
- Tootsie role, anybody? While Dustin Hoffman starts out playing a female simply in order to get work, he ends up playing the part in real-life as well.
- In The Crying Game, an IRA-terrorist falls for a cross-dresser named "Dill," only to find out too late that Dill has a pickle— after they had sex.
- In Trainspotting, Begbie makes out with a "woman" in his car for a while before discovering it's a man.
Literature
- George, from the otherwise hilariously backward children's series The Famous Five by Enid Blyton.
- Min (a woman) in the Wheel Of Time books wears men's clothes, which in her own medieval-esque society is quite shocking. Once said society gets used to the idea, women wearing pants becomes a fashion statement.
- Polly from Monstrous Regiment along with nearly every "female" character in the army. After a while it gets a bit silly.
- Salome "Sam" Fredericks in Tad Williams' Otherland series pretends to be a boy online, complete with Tomboyish Nickname, to avoid getting singled out for her gender. This causes complications when her friend, Orlando Gardiner, seeks her out in Real Life.
- The briefly-appearing "Lillie Longtree" in Welkin Weasels: Vampire Voles is an actor who usually plays female roles, and wears a red riding hood when out walking in the forest "to confuse the beasties". It should probably be noted that Maudlin asks about this "with a touch of envy in his voice".
- Hello, Eowyn from Lord Of The Rings?
- The medieval Arab and Turkish epics were replete with crossdressing — both males as females and females as males. The legendary hero al-Battal crossdresses to sneak into the Greek emperor's palace, and his son Madhbahun disguises himself as a princess to lure the wily villain Uqba into his clutches. In Sirat Dhat al-Himma, the Muslim warrior queen dresses up as a priest and kisses the Greek princess Nura.
Live Action TV
- Max Klinger on MASH was a wholesome, if definitely not attractive or believably female, crossdresser.
- Klinger was only feigning insanity to get a Section-8 discharge from service. When Radar left, Klinger became clerk and dropped his cross-dressing gig.
- Although, having worn women's clothing for so long he found that his body had gotten used to the feel and he developed a rash unless he wore female underwear under his uniform. There was a kind of 'don't ask-don't' tell policy about it.
- On Hill Street Blues, Jeffry Tambor played a cross-dressing lawyer who was doing so on advice from his psychiatrist to "resolve his feminine-identity issues." (The "cure" worked, and the same lawyer later became a highly-respected judge on the series).
- DEA Agent "Denise" Bryson on Twin Peaks, played by David Duchovny. (Who, as it turns out, has really nice legs.)
- Reality TV example: Derrick Barry of America's Got Talent
- Clarence from Boston Legal crossdressed as both an alter ego, Clarice, and Oprah.
- How is Steve from The Drew Carey Show not on here?
- Tetsu/DekaBreak in Tokusou Sentai Dekaranger seems inordinately fond of dressing up as a woman during undercover missions. Both times he's done it, he's caught the eye of a creepy buglike minor criminal stalker...who didn't care that it was a trap when Tetsu revealed his true gender.
- Johnny Depp's attraction to eyeliner didn't start with Captain Jack Sparrow - waaay back during 21 Jump Street, he was undercover in drag in "In the Custody of a Clown
 " and looked far too convincing.
- Subverted in ''Leave it to Beaver," where Wally is cast to play a saloon-girl in a "Summer Stock" Western; he hates the idea so much, that he ends up conning the perfect person for the role into taking it— Eddie Haskell.
- Also subverted in Comedy Central's series Strip Mall, a male character is seduced by a supposed cross-dresser (but who is actually played by a very obviously female woman).
Music
- The protagonist of the song "Cherry Lips" by Garbage.
- As quoted at the top of the page, "Lola" by the Kinks.
- Desmond, the family man who "stays at home and does his pretty face" in "Ob-La-Di, Ob-La-Da" by the Beatles.
- The titular character in Pink Floyd's first single, Arnold Layne.
Theater
- William Shakespeare's comedies employ this trope rather often, making this older than steam.
- This was due to the fact that women weren't allowed on stage by law, so female roles were played "in drag—" the very phrase "in drag" may originate from theater, to describe the fact of men in dresses that dragged on the stage.
- Angel from Rent.
- Middleton and Dekker's 1610 comedy The Roaring Girl features one of these as a protagonist; unlike the cross-dressing heroines of Shakespeare's plays, though, she isn't disguised, and everyone in the play knows her real sex — she just likes dressing like a man. (The real person she is based on was slightly less wholesome.)
- Modern productions of Peter Pan often have Peter played by a woman, since the character is eternally young and shouldn't have a grown male's voice. The actress will sometimes reveal her gender at the curtain call.
Video Games
- Bridget from Guilty Gear. The original story was that Bridget is part of a set of identical twins, which in his village were considered bad luck, and was sent to be a nun, therefore his whole story path is him wanting to prove he wasn't a bad omen or anybody. His creator admits that making him a boy was, in the spirit of other characters in the game, to simply make him more interesting.
- The most disturbing part about this is that Bridget crossdresses to the point of seemingly wearing female underwear.
- The character of Vivian in Paper Mario: The Thousand Year Door was, in the Japanese version, a male who appears female. In fact, the likeness was so good it took only a few text edits to scrub out the potentially offending element. Ironically, not many characters in the game even have features; Vivian himself is a faceless spectre with a big hat, lipstick, and curly hair.
- And the original manual for Super Mario Bros 2 (the U.S. one) gives this Birdo description: "He thinks he is a girl and he spits eggs from his mouth. He'd rather be called 'Birdetta.'" Much like Vivian, in later games in the U.S. she's retconned into a girl, but in Japan s/he's a guy. Much more recently however, Nintendo of America has inched a bit closer to recognizing this issue.
- Although not actually crossdressing, Lucius (a very androgynous man in unisex clothing) from the 7th Fire Emblem otherwise fits this trope, including people getting squicked out at him when the learn his true gender.
- Persona 4 Naoto is a reverse trap.
- Another example would be Human Teddie, who can pull off cosplaying Alice.
- The Magypsies in Mother 3, and, to a lesser extent, the girl they raised, Kumatora. Noticeably, the only Magypsy who doesn't crossdress is a traitor.
- Faris from Final Fantasy V. One character even mocks her by saying, "We will fight like men! And women! And women who dress like men!" It doesn't help that she's probably the most masculine-acting of all of the player characters. The main character even mistakes her for a man.
- Sheik, who is secretly Princess Zelda in disguise from Legend of Zelda is a pretty famous one, to the point where it's a You Should Know This Already.
- From Suikoden V, Rahal dresses up as his sister to distract some guards. Those guards were not the only ones distracted.
- In Pokemon Crystal , if you choose the female trainer, the overworld sprite changes from female to male if you do any game link cabling with any of the other six games. Yes, even with another Crystal version.
- In Animal Crossing, you can wear any clothing or accessory items, even those that are obviously intended for the opposite sex. This extends in more recent versions of the game 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.)
Web Comics
- Tip Wilkins from Skin Horse is a cheerful Casanova in a dress. He's fashion conscious and uses a variety of complex female outfits, but he makes no attempt to appear female (although given the art style, it can be a bit hard to tell). This is some kind of strange self-flagellation on part of the artist, whose previous Narbonic starred four obsessives who didn't always keep track of whether they were wearing pants.
- Of course, it's also part of the WizardOfOz motif, specifically to Princess Ozma.
- Magical Transvestite Cherry from Footloose, described on the cast page as "the only Magical Girl with a shred of humanity."
- Paul "the transvestite stalker" from College Roomies From Hell!!! - granted, a bisexual prostitute and a bit of a harasser, but still a generally positive influence on the cast once he becomes a genuine character rather than a Running Gag, serving as the voice of reason essentially whenever he plays a significant role.
- Material Girl features a teenager forced into this.
- Maxine/Max of "Art School Sub Rosa" is a female who's attending Art school as a male as part of a somewhat crooked "deal" to get a scholarship.
Web Original
- Agent Drake of Protectors Of The Plot Continuum doesn't do this regularly but has demonstrated that he has no problem with wearing a harem girls' outfit, and in fact seemed decidedly, erm, interested by it. Of course, for most of the time he was wearing it, he was transformed into a woman, so technically that wasn't crossdressing, but when he changed back he was still in the skirt and not in any hurry to get out of it.
Western Animation
- Bugs Bunny, when he's trying to trick someone.
- Pleakley in Lilo And Stitch and Lilo And Stitch The Series.
- justified in that having three legs pretty much rules out pants as an option.
- And Jumba, to an extent. In the series he once dressed up as Pleakley's 'bride' and nearly married him.
- In Rockos Modern Life Heffer's stepbrother Peter seemed to like to wear cheerleading outfits and ballerina tutus.
- In The Simpsons, Veronica in the episode There is Something About Marrying, the character who was going to marry Patty.
- Timon of The Lion King ends up in a skirt in one scene ("What, you want me to dress in drag and do the hula?"), though since the animal characters don't normally wear anything it's debateable as to whether this counts.
- Part of Override's bio from her toy on Transformers Cybertron (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.
- Jerry from Tom And Jerry also cross-dressed a few times to trick Tom, who apparently is less likely to be violent towards a girl mouse.
- An episode of The Fairly Oddparents has Chester dressing up as a girl so he can get a skating partner.
Real Life
- David Bowie looks simply marvellous◊ in a dress.
- Sure, he was responsible for some of the worst cinema ever committed to celluloid, but Ed Wood was also a patriot, a war hero, was very respectful to ladies, treated his troop of freak actors as equals, and provided Bela Lugosi with steady work when no one else would.
- Many real-life crossdressers work this way, being fairly normal people other than their crossdressing.
- Arguably, the entire Glam Rock movement qualified.
- Everyone in the first part of the Queen video I Want To Break Free. Roger Taylor looks surprisingly good in a schoolgirl outfit, by the way.
- Tomboys, and many other women in Western society.
- Eddie Izzard is this, and often mentions in his comedy shows that he is an executive/action transvestite, not a weirdo transvestite.
- Possibly Mana and many other J-rockers. Mana has toned it down a little in recent years, but is still one of the most convincing crossdressers in J-rock.
- Hizaki◊ from Versailles gets special mention, though. This troper thought he was a really pretty girl. (Yeah, that's seriously a guy.)
- Danny Bonaduce was seduced by a cross-dresser, and found out only too late— just as the cross-dresser likewise found out too late that Danny was a psychotic ex-child star and martial-arts/steroid freak. Bonaduce spent time in jail, and the cross-dresser spent time in the hospital.
- Pete Burns.
- Would he really count as "wholesome", though?
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