In anime (as in life), sometimes the guys are cute and the girls are cool. And sometimes they like to wear clothes that highlight that fact.
Usually, the results are excellent. Here are the 10 best crossdressers in anime.
Oh, and keep in mind – the reveal of a character’s true gender tends to be a big plot twist in a lot of these. Be prepared for potential spoilers throughout.
Anime "Best of" Genre List
Seishirou Tsugumi (Nisekoi)
Tasked with guarding her friend Chitoge Kirisaki, Seishirou Tsugumi was trained from childhood to be a trained hitman.
Tsugumi’s mentor, Claude, raised her as a boy, gave her a boy’s name, and even now doesn’t know she’s actually a she. Given the fact that she has the biggest boobs of anyone in the series, obviously chest wraps are involved.
She still wears the boys uniform to school, but her friends gave her a hair bow to make her look more feminine.
Haruhi Fujioka (Ouran High School Host Club)
Haruhi Fujioka isn’t really concerned with her gender. She made it to the ultra-elite Ouran High School on the strength of her brains alone, and isn’t concerned with the opulent lifestyles of those around her.
But after damaging some expensive property, she finds herself not only working for the campus’ host club, but doing so as a host herself.
So Haruhi’s job isn’t just to dress as a boy, it’s to seduce other girls in the process.
Kenjiro Hato (Genshiken Nidaime)
Kenjiro Hato is conflicted about his identity. He feels comfortable dressed as a girl, but feels it’s indecent to do so. He insists he isn’t homosexual, but enjoys drawing homoerotic comics.
He is timid and unconfident, especially when dressed as a boy, and the examination of his character in Genshiken Nidaime makes Hato of the more interesting examples of the “trap” character.
Mariya Shidou (Maria Holic)
Mariya Shidou is a boy attending an all-girls school. His sister, Shizu, is a girl attending an all-boys school.
Why? Mariya’s grandmother is the head of both schools, and made a bet that if either of them can get through all three years of high school without revealing their gender, they would get to take over both schools.
Mariya comes off as kind and compassionate, but he is actually conniving and sadistic, and gets his kicks from being a bully.
Hime Arikawa (Himegoto)
Hime Arikawa is definitely a boy. He even likes being a boy. But his parents put him in deep debt, and with nowhere to turn, he gets help from the Shimoshina High School student council.
They save him from his debt, but in return, Hime must dress as a girl and become the “dog” of the student council for the remainder of his high school life.
Naoto Shirogane (Persona 4: The Animation)
Ace detective Naoto Shirogane can typically be seen wearing the boys school uniform around Inaba as she works with the Investigation Team to solve the string of bizarre murders plaguing the town.
Naoto struggles with her sexuality and masquerades as a boy because it’s more difficult for her to earn respect as a female detective (especially given her young age).
Sister (Arakawa Under the Bridge)
Not every cross-dresser has to be androgynous. Sister is a 29-year old, English, gun-toting former mercenary. He is absolutely a man in every way, and towers over everybody in Arakawa’s strange bridge.
And now he dresses like a nun, which is why the village chief called him “Sister.” I don’t believe this is explained any further.
Chihiro Fujisaki (Danganronpa)
Not only does Chihiro look like a cute girl, he is also tiny, even among the other girls. He quietly struggles with his gender identity until his gender reveal serves as the turning point of Danganronpa‘s second case.
Chihiro is also an expert hacker who is able to create an AI version of his consciousness to help out his friends.
Ruka Urushiba (Steins Gate)
Ruka Urushiba isn’t at all conflicted about his gender identity. He’s absolutely certain he wants to be reborn as a girl.
Incidentally, Ruka’s voice actress in Japan, Yuu Kobayashi, also played Mariya Shidou in Maria Holic. Perhaps she’s a specialist in playing androgynous men.
Tsukimiya Ringo (Uta no Prince-Sama)
Tsukimiya Ringo the “crossdressing idol” is a teacher in Uta no Prince-Sama, whose job is it to teach the attractive men in A Class. He went into crossdressing as a response to his agency’s insistence that he act more feminine to match his cute appearance.
Fun fact: the pink hair is actually a wig. Also, he plays the clarinet.