http://tvtropes.org/pmwiki/pmwiki.php/Main/WholesomeCrossdresser

"Uh... Olsen, when we said that this story would call for staking out Luthor in 'casual dress'..."

Ed Wood: I like to dress in women's clothing.

George Weiss: You're a fruit?

Ed Wood: No, not at all. I love women. Wearing their clothes makes me feel closer to them.

George Weiss: You're not a fruit?

Ed Wood: No, I'm all man. I even fought in W.W.2. Of course, I was wearing women's undergarments under my uniform. Ed Wood I like to dress in women's clothing.You're a fruit?No, not at all. I love women. Wearing their clothes makes me feel closer to them.You're not a fruit?No, I'm all man. I even fought in W.W.2. Of course, I was wearing women's undergarments under my uniform.

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Crossdressing characters who are presented in a positive (or at least neutral) way. Frequently presented as attractive (or at least not unattractive), relatively "normal" people as opposed to perverts or sexual deviants.

The Wholesome Crossdresser may be of any sexual orientation, but in settings where being straight is considered part of being "normal," one can expect to see the character's heterosexuality explicitly highlighted.

Some permutations of the trope are more or less unique to Japanese works. The Japanese Wholesome Crossdresser is usually well-groomed, compassionate, nice, and above all, so convincing that their sex is only mentioned on occasion, as a reminder to newer members of the audience. There's a fair chance someone will get a crush on them, although this is usually resolved after The Reveal.

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The opposite of Creepy Crossdresser. May overlap with Disguised in Drag or its Distaff Counterpart, Sweet Polly Oliver. (If the character wears cross-dressing disguises more often than seems strictly necessary, this trope may apply.) Wholesome Crossdressers tend to enjoy dressing, even if only reluctantly, secretly, or subconsciously.

Often overlaps with Drag Queen (a campy, hyper-feminine form of expression with heavy ties to gay/bi male culture), but usually doesnt with being Transgender (an intricate subject that is more connected with inward identity than outward appearance).

Compare Otokonoko Genre, which is about male crossdressers (and occasionally Transgender women), that are almost always presented as wholesome.

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Examples:

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Anime & Manga

Comic Books

Fan Works

Films — Animation

In Pinocchio and the Emperor of the Night, Scalawag and Igor use cross-dressing in an attempt to save Pinocchio from his illusion.

The title character in Mulan is disguised as a male in order to replace her sickly father during a war.

Lilo & Stitch: Pleakley is a textbook example of this trope as most of his disguises on Earth consists of women's clothing. He has grown comfortable in this and has done this very frequently. Jumba cross-dressed once in the series in a bridal gown in a sham marriage with Pleakley in order to please Pleakley's mom. The marriage itself was called off meaning that Jumba and Pleakley currently remain unmarried.

The title character of Rango wears a dress in order to pass as a travelling actor to get some arrest-ees to let their guard down. It turns into an elaborate wagon chase scene, with him still in the dress.

Films — Live-Action

Literature

Live-Action TV

Music

Myths & Religion

Pro Wrestling

" The Crush Girls 25th Anniversary Memorial Match" at NOSAWA Bom-Ba-Ye #5 Rongai One Night Stand saw Yoshihiro Takayama and Minoru Suzuki dressed as Lioness Asuka and Chigusa Nagayo against Kikutaro and Yoshihiro Sakai dressed as Dump Matsumoto and Bull Nakano.

Dramatic Dream Team: Rookies Shun Miyatake and Hiroshi Fukuda were made to dress like women and to entrances of Kazuki Hirata and Magnum HIRATA.

Tabletop Games

Exalted has a few cultural examples as part of the background: In the West are the Tya, a "third gender" of women who adopt male social roles in order to work as sailors. This is mainly because the waters of the West are overseen by hag-like spirits known as storm mothers, who will try to sink any boat that's crewed by any woman prettier than themselves. Which is pretty much every mortal woman in Creation, and most of the dead ones. The city of Chiaroscuro is overseen by the Delzahn, who are pretty firm on gender roles - men defend and supply the household, women run it but don't do much on the outside. However, it allows men and women the option of becoming Dereth - they basically can dress and act like the other gender, as long as they wear a gray sash at all times in order to avoid confusion.

The Howling Banshees, an Eldar warrior Path in Warhammer 40,000 are traditionally an all female squad. Males, however, are permitted to join their ranks. Since the Banshee is a female spirit in Eldar mythology, he adopts a female persona and female armor when wearing his 'Warmask'.

Theatre

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.) Angel Dumott Schunard from RENT, who may also be Transgender. It's kinda hard with Trans Equal Gay thing that's there.

Fancourt forced to chaperone as the titular Charlie's Aunt.

Video Games

Visual Novels

Web Comics

Web Animation

As this page from the wiki demonstrates, every main character (and then some) from Homestar Runner has crossdressed at least once, with the sole exception of Bubs.

Web Original

Web Videos

Western Animation

Real Life