Anime have never shied away from the cross-dressing culture. Be it for self-expression, comedic, or serious purposes, it always had characters who were into crossdressing.

There have been many negative prejudices related to this kind of lifestyle that needs to be addressed. What’s better than to learn more about this by watching anime? Here is the list of the top 10 Anime that explore the nuances and struggles of cross-dressing.

Lifestyle 10. Revolutionary Girl Utena

This magical girl anime is known for its unique twist on the typical shoujo genre. Revolutionary Girl Utena is praised for its bold portrayal of themes such as LGBT and coming of age.

The series protagonist, Utena Tenjou, crossdresses and adopts a more boyish personality in order to become her ‘prince.’ She absolutely hates any type of feminine or formal clothes and prefers to dress in whatever makes her more comfortable.

Lifestyle 9. Wandering Son

Wandering Son, written by Takako Shimura, follows the budding friendship of two trans characters, Shuichi and Yoshino. This series is praised for its realistic depiction of transgender individuals and gender dysphoria.

Shuichi and Yoshino were both struggling with their respective gender identities and societal expectations. Shuichi is a trans girl who soon starts crossdressing to express herself, and Yoshino is a trans boy who is often seen as wearing more masculine clothes.

Lifestyle 8. Pretty Boy Detective Club

Based on the original Japanese novel series by Nishio, Pretty Boy Detective Club follows a middle schooler, Mayumi Dojima, who wishes to become an astronaut. She makes a bet with her parents to find the star or to quit her passion.

Mayumi Dojima then cross-dress to enter the Pretty Boy Detective Club for a celestial case. This anime is an enjoyable combination of mystery and crossdressing wrapped in stunning animation and exquisite visuals.

Lifestyle 7. Maria Holic

Maria Holic by Minari Endo is one of the best series if you want to enjoy a twisted romantic comedy. Kanako Miyamae is searching for her ‘princess’ in her all-girls high school. But her ideal partner turns out to be a cross-dressing boy!

Mariya Shido, who had earned the affection of Miyamae, is actually a sadist behind his playful demeanor. He dressed as a beautiful girl to win the chairmanship of both all-male and all-female schools.

Lifestyle 6. Stop!! Hibari-kun!

Stop Hibari Kun! by Hisashi Eguchi is for those who want to enjoy the chaos of a normal boy living with a Yakuza and his four children. The series holds a record for being the first anime to feature a cross-dressing main character.

Hibari Ozora, the daughter of the Yakuza, even though is a male, has a desire to be a female. She fearlessly embraces her feminine side despite the societal hurdles she faces daily.

Lifestyle 5. Mayo Chiki!

Mayo Chiki! is a fun, romantic comedy about a high school student with gynophobia who finds himself in a tricky situation after accidentally stumbling upon a big secret.

The series’ character, Subaru Konoe, is a handsome and elegant butler for the principal’s daughter. But behind her disguise, she’s actually cross-dressing as a boy. If you’re a fan of harem and fanservice, this series should be on your watchlist.

Lifestyle 4. Princess Jellyfish

Princess Jellyfish, based on the manga by Akiko Higashimura, is a short anime series that revolves around an apartment building and its tenants, Otaku women’s lives.

Kuranosuke, a resident in that apartment, loves to crossdress despite facing resistance from his family. He also uses a feminine alias and is popular with the girls who find him cool. This slice of life is a must-watch for its soothing touch on self-discovery and coming-of-age themes.

Lifestyle 3. Princess Princess

Princess Princess is one of the best anime with cross-dressing as its core theme. Originally written by Mikiyo Tsuda, the story follows the three high school boys selected to be the ‘princess’ at an elite all-boys high school.

The series protagonist, Toru Kouno, happily takes up his new duty and seeks solace from his problems. The ridiculous story is like a breath of fresh air with all the likable main characters and 10/10 belly-hurting comedy.

Lifestyle 2. Senpai is a boy

The new gen crossdressing anime that is quickly becoming the weebs community’s new favorite. This slice-of-life romantic series follows Saki Aoi, who confesses her feelings to her senpai, Makoto Hanaoka.

But here’s the twist! Makoto, who is thought to be a beautiful girl by Saki, is actually a cross-dressing boy! But you know what? Saki doesn’t care about it either way, as she is now more enthusiastic than ever to become his first love. But maybe Saki is someone Makoto needs to brighten his depressing life.

Lifestyle 1. Ouran High School Host Club

No doubt, this classic shoujo anime is the best cross-dressing anime, and no weeb will argue about this. Ouran High School Host Club is a humorous tale about Haruhi Fujioka, who starts to work in the school’s popular host club as a way to pay off her debt.

Ouran might be the first anime that breaks itself from the mold of stereotypical cross-dressing anime cliches. Haruhi is confident about her gender identity and wears whatever she’s comfortable with. Apart from that, the series is a must-watch for its soundtrack and lovable cast.

So, these are the top 10 cross-dressing anime that anyone interested in this genre should watch. If you have any more recommendations like these, feel free to give your names in the comments section.