Top 10 Best Anime Crossdressers

Well, I was looking at my other list and just wanted to make another anime one. I'm not overly fanatic about anime crossdressers, but sometimes they make me smile or be like, That's a boy/girl!

Shorter comment sections than before, though. Anyway, enjoy!

Spoilerish

The Top Ten

Haruhi Fujioka (Ouran High School Host Club)

Haruhi Fujioka is the main character in the manga and anime series Ouran High School Host Club, created by Bisco Hatori. She is a scholarship student at the elite Ouran Academy and accidentally becomes a host club member after being mistaken for a boy. Haruhi challenges gender norms throughout the series... read more

OK, Haruhi is second because she's both pretty and handsome at the same time. I've always thought she looked a little girly in her guy get-up, but I really like her nonetheless. It's kinda similar to how you dress a younger brother up in a princess dress and crown!
Tsukimiya Ringo (Uta no Prince-sama)

I recently got into Uta no Prince-sama, and I know all the characters here except Juliet, Nagisa, and everyone below Aoi.

I really, really thought that he was a she. He's just so pretty! For some reason, I really like his pink, wavy/curly hair, and he can even rock a turtleneck sweater. I don't know, he's just a nice cross-dressing character.
I really thought he was a girl. It was like, What!?
Grell Sutcliff (Kuroshitsuji)

Grell Sutcliff (Japanese: グレル・サトクリフ, Gureru Satokurifu) is a major antagonist in the manga and anime series Black Butler. She is a part of the Retrieval Division of the Grim Reaper Dispatch.
Grell initially posed as Angelina Dalles's butler and conspired with her as Jack the Ripper. As a result... read more

I personally like Grell. He's bat crazy, weird, and loves the color red! At first, I just thought he was a kinda weird looking anime dude, but then I learned he was a gender-swapping reaper. Surprise, surprise!
Kaoru Hitachiin (Ouran High School Host Club)

Yeah, I know, "Why so much Ouran High School Host Club?" To be honest, I don't really know. I guess I just like their cross-dressing. And why the twins? Well, you have to admit, they were adorable as little girls, and you shared Haruhi's reaction when they were older.
Hikaru Hitachiin (Ouran High School Host Club)
Izumi Sena (Love Stage!!)

Izumi Sena (Japanese: 瀬名泉水, Sena Izumi) is the main protagonist of the anime and manga series "Love Stage!!". He is a college student who dreams of becoming a manga artist.
His relationship with Ryouma Ichijou, another important character in the series, plays a central role in the plot. This... read more
Hitoshi Sugoroku (Nanbaka)
Ciel Phantomhive (Kuroshitsuji)

Earl Ciel Phantomhive (Japanese: シエル・ファントムハイヴ, Shieru Fantomuhaivu) is the main protagonist of the manga and anime series Black Butler. He is the current head of the Phantomhive house, the notorious Queen's Watchdog, the owner of the Funtom Corporation, and an Aristocrat of Evil.... read more

What? He makes a very pretty girl. Prettier than most I know. But he has the reaction to cross-dressing that I'd have if I did it.
Eh. This is so wrong/weird feeling! Do I have to?
Marulk (Made In Abyss)
Juliet (Romeo x Juliet)

I honestly preferred her as the Red Whirlwind. Yes, she was nice as a girl, but she was a hero as the Red Whirlwind.
But the part where Romeo finds out she's actually a girl is kinda...awkward...

The Newcomers

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Mare Bello Fiore (Overlord)
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Felix Argyle (Re:Zero - Starting Life in Another World)

The Contenders

Ryoji "Ranka" Fujioka (Ouran High School Host Club)

Because it's not enough having a daughter dress like a boy, you need to have the dad dress like a lady, too! Maybe it's that irony that made me add him or because he's like a roll-up of both mother/father for Haruhi who needs that.
Go Ryoji!
Rui Ninomiya (GatchaMan Crowds)
Nagisa Shiota (Ansatsu Kyoushitsu)

Nagisa Shiota is one of the students in Class 3-E, the main student protagonist, and the narrator of the anime and manga series Assassination Classroom. He is known for his calm demeanor and exceptional assassination skills. Throughout the series, he grows in confidence and plays a key role in the story's... read more
Nelli Pepper (Tegami Bachi)
James (Pokémon)

In all their disguises, James has cross-dressed several times: the bikini-like outfit, magician assistant, ballerina princess, and hula girl. Do you remember the schoolgirl costume? I do!
Anyway, having liked Pokémon for so long gets James on the list. He's also a funny character and one of my favorites.
Emporio Ivankov (One Piece)

Emporio Ivankov, or Iva for short, is the "Queen" of the Kamabakka Kingdom, known as the "Okama King" and a "Miracle Person." He is an officer of the Revolutionary Army in the manga and anime series One Piece. Ivankov possesses the Horm-Horm Fruit, which grants him the ability to manipulate hormones... read more

I love One Piece. Of course, I'm going to add a character in! And who is better than the Queen!
(If you know someone better, then add them!)
Midare Toushirou (Touken Ranbu)
Hideyoshi Kinoshita (Baka and Test)
Chihiro Fujisaki (Danganronpa: Trigger Happy Havoc)

What I specifically love about him is that he had a completely valid reason as to why he cross-dressed, instead of it being played off as a gag.
Joey Jones (Heroman)
Legoshi (Beastars)

Legoshi, also referred to as Legosi depending on the translator (Japanese: レゴシ, Regoshi), is a male gray wolf and the main protagonist of the Japanese manga and anime series Beastars. This series is written and illustrated by Paru Itagaki.... read more
Lag Seeing (Tegami Bachi)

Lag Seeing (Japanese: ラグ・シーイング, Hepburn: Ragu Shīingu) is a Letter Bee and the main protagonist of the anime and manga series Tegami Bachi by Hiroyuki Asada. He is voiced by Miyuki Sawashiro. Lag is a young boy with a very focused mindset. Regardless of the situations he gets into, he always focuses... read more
Aoi Hyoudou (Kaichou Wa Maid-Sama!)

Once again, I thought he was a she. Why must I always do that? But I guess that's the purpose of cross-dressing. Anyway, he's a very cute girl and boy! Win, win, right?
Does he make anyone else think of Elizabeth when he's cross-dressing and Ciel when he's not?
Tughril Mahmut (Altair: A Record of Battles)
Ritsu Sohma (Fruits Basket)