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 crossdressing disguises more often than seems strictly necessary, this trope may apply.) Wholesome Crossdressers tend to enjoy dressing, even if only reluctantly, secretly, or subconsciously.

Generally does not overlap with Drag Queen (which is more about "performance" and theatricality) or being Transgender (usually a much deeper and more complicated subject), though there are exceptions.

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 and Manga

Comic Books

Fan Works

Films — Animation

In Pinocchio and the Emperor of the Night, Scalawag and Igor use crossdressing 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.

Tokyo Godfathers' Hana is a woman who insists that "God made a mistake" by putting her in the body of a man. In fact, a former professional drag queen, and probably the best groomed of the homeless bums who are our heroes — also the first to take the Trash Bin Baby to heart. Has an extremely Girly Run and a bass voice.

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 into 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

Manhua

Xiao Meng the eunuch assassin from Chinese manhua Ravages of Time insists he's a man, but specializes in disguising himself as a woman.

Music

The protagonist of the song "Cherry Lips" by Garbage.

"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. Funnily enough, that lyric was a mistake made by Paul, but they left it in because they were sick of working on that song.

Pretty much everyone in Queen, in the video for "I Want to Break Free". Nice legs, Roger Taylor.

"Bitty Boppy Betty" by Pink Martini is about a charismatic district attorney who dresses as a woman on the weekends, and who is the toast of her local nightclub: "You really can't ignore her,

And if you don't adore her,

There might be something wrong with you!"

Green Day's "King for a Day" (Princess by dawn!). "Who put the drag in drag queen?

Don't knock it until you've tried it"

Vocaloid: Kagamine Len is this in "Imitation Black" and other Visual Kei styled songs by natsuP. He is in "Servant of Evil," despite the title, he's a Love Martyr who crossdresses to pull a Twin Switch to keep his evil sister from being beheaded. Kaito in "The Madness of the Duke of Venomania" does this to trick and kill Gakupo, who's been luring innocent women into his harem.

The UTAU Ritsu Namine. How wholesome he is depends on how he's played, considering the fake breasts in his dress are working missiles.

The protagonist of Placebo's song "Nancy Boy".

"Rosie" by Joan Armatrading.

Florence Welch wears a suit both in the 2008 video for "Dog Days Are Over", and in the "Sweet Nothing" video.

Mythology

Professional 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.

Religion

Deuteronomy 22:5 defies this trope severely: "The woman shall not wear that which pertaineth unto a man, neither shall a man put on a woman's garment: for all that do so are abomination unto the Lord thy God."

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'.

Theater

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.

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

Video Games

Visual Novels

Web Comics

Web Original

Western Animation

Real Life