Princess Jellyfish focuses on the life of Tsukimi, an aspiring illustrator living in Tokyo in an all-female otaku house, Amamizukan. Each one of their group has a specific passion. For instance, Tsukimi has been obsessed with jellyfish since she was a child and is dreaming of creating a beautiful jellyfish-like dress. Things take an unexpected turn when Kuranosuke shows up in her life, a wealthy student who loves crossdressing in stylish outfits. Kuranosuke, who has a great eye for fashion and all things beauty, takes an interest in Tsukimi and helps her achieve her dreams. Conflict ensues when the reclusive lifestyle of the female otaku gang gets disrupted by the presence of the model-like Kuranosuke in the guise of a beautiful girl (no one else except for Tsukimi knows his true identity).

Princess Jellyfish is unique in showing us a shoujo heroine, Tsukimi, who defies gender expectations. Even though a big part of the surprise factor is Tsukimi’s transformation in Kuranosuke’s hands, we are never given the impression that this is the end goal. Princess Jellyfish shows Tsukimi changing back to her normal tracksuit attire and glasses as soon as she is done with work. Looking fashionable is just a costume to achieve her vision. Similarly, Kuranosuke loves taking care of his appearance and never backs down to his father’s complaints, wanting him to dress in masculine clothes. Overall, Kuranosuke’s attitude is depicted in a positive light, never played for laughs, which is a breath of fresh air.

Yuuri Katsuki is the most promising figure skater in Japan. After he gets crushed at the Grand Prix, he loses his motivation and goes back to his hometown. Yuuri struggles with crippling anxiety and self-doubt, but he is not fully aware of the extent of these issues. One day, a video of Yuuri performing a routine of famous ice-skating veteran
Victor Nikiforov gets viral. Victor himself tracks him down and asks Yuuri to become his coach. This is how an intense collaboration begins, which evolves into a more intimate relationship.

Yuuri struggles with his confidence and self-image, using food as a coping mechanism. As a figure skater, Yuuri has to show strength and grace - it is not just a matter of performing choreography but also connecting with it on a deeper level. This is where Victor’s influence comes into play, as he challenges Yuuri’ to show his passionate side. Under Victor’s wing, Yuuri connects with this part of him, which is usually associated with female characters, and he becomes the audience’s sweetheart. Yuri!!! on Ice, even though it is a sports anime, doesn’t focus on super-competitive, often macho characters but Yuuri’s self-development and reconnection with himself.

Fruits Basket tells the story of the Souma family: in each generation, twelve Sohmas are born under the curse of the Zodiac. This means that when hugged by a member of the opposite sex they turn into the Chinese zodiac animal’s spirit that they were cursed with. Tooru Honda, one of the most kind-hearted shoujo protagonists in history, gets to live with three members of the Souma family, two of which are her classmates and sworn enemies: Yuki, possessed by the Rat, and Kyo, possessed by the Cat, the Zodiac outcast. Under Tooru’s influence, the Soumas begin to open up, but the curse is not easy to break: there is Akito, the sadistic head of the family, who holds great power over the Souma Clan.

Fruits Basket has several characters that defy gender expectations. Ayame, Yuki’s flamboyant older brother and the Zodiac’s Snake, runs his own business which sells women’s clothes that are also worn by men, including himself. Ayame is never apologetic about his passion. He doesn’t even understand why Yuki is embarrassed of his older brother when he shows up in a beautiful lolita dress. There’s also Momiji, the Rabbit, who prefers wearing a girls’ school uniform because it’s cute and it suits him. Finally, Ritsu, the Monkey, is a soft-spoken yukata-clad young man who is always mistaken for a woman because of his choice of attire and feminine manners.

Kino’s Journey follows Kino, a young woman on her talking motorcycle Hermes, as she travels through different countries, each with its peculiar customs. Kino looks agreeable and she does try to blend in with the local population at each of her stops, but she is also prepared for danger, always carrying her two guns. Kino has to use her wit, her weapons, or both to get out of complicated situations, as she is faced by strange dilemmas: What is right in one country might be a grave crime in another. Along the way, Kino discovers more about herself, what she values, and deals with her past.

Kino’s wanderlust is so strong that she never stays in a country for more than three days. Usually, on the third day, the true nature of the place is revealed and her neutral stance comes in conflict with her sense of justice. A mysterious MC, Kino doesn’t want to reveal her past. Her androgynous looks lead most to mistake her for a guy and she rejects standard ways of addressing herself, as a “miss” - she is just Kino. Kino’s Journey is an anime with philosophical undertones and deals with several questions through Kino and the people she meets along the way, such as the right to self-determination.

This is a classic and probably how many die-hard otaku first got into anime, but it is definitely worth a revisit. Chihiro is moving with her parents. Eventually, the family stops at an inn along the road and Chihiro’s parents begin gorging on a huge feast. They are turned into pigs by witch Yubaba and Chihiro is forced to work at her bathhouse, in the spirit realm. There, Chihiro meets strange and captivating creatures, like elusive yet caring Haku, and Kaonashi, a gluttonous spirit who eats everything that passes him by. With wit and courage, Chihiro overcomes the challenges and grows as a person to save her parents.

Chihiro is a 10-year-old with more grit and brains than the adults in her life. Director Hayao Miyazaki is known for creating strong female leads in his movies. Haku is there to help Chihiro, but he is not Prince Charming: Chihiro calls the shots and she even saves Haku from Yubaba’s curse. In Hayao Miyazaki’s words: “Many of my movies have strong female leads—brave, self-sufficient girls that don't think twice about fighting for what they believe with all their heart. They'll need a friend, or a supporter, but never a savior. Any woman is just as capable of being a hero as any man.”

Speaking of Prince Charming, who needs one when the bed is so soft and the princess just wants to sleep…? A Sleeping Beauty fable in an alternate universe, Sleeping Princess introduces us to Princess Aurora (Disney reference anyone?) who is captured by Demon Lord Tasogare. Princess Aurora doesn’t care about escaping, she is more preoccupied with finding the perfect pillow, the softest mattress, and the comfiest duvet. With Demon Castle, well, being a Demon Castle, such comforts are hard to find. This is why Aurora has to improvise! Armed with a giant pair of scissors, the princess goes around the castle terrorizing demons three times her size.

If it’s not clear why Sleepy Princess defies gender expectations by now, let’s give you a scene: Imagine a cute long-haired girl sleeping blissfully in her bed. She gets up looking bored and unimpressed. Princess Aurora hits her brush on her jail bars and the cute debi akuma—a fluffy teddy bear with bat wings supposed to keep watch on her—flies her way with shining eyes. After getting brushed, it gives her the key to her cell! Princess Aurora goes on to hunt monsters to turn into a pillow, while the Hero’s party is on their way to save her. Aurora is not a damsel in distress but a cunning character who can save herself but is too sleepy to care!

Based on the award-winning manga series by Shimura Takako, Wandering Son introduces us to two young gender non-conforming students. The show is positive and realistic towards people who might not feel comfortable with the gender they were assigned at birth. As they go through adolescence, Shuuichi and Yoshino realize that they don’t feel right in their skin. Shuuichi starts wearing dresses and wigs, turning into a cute girl; Yoshino is tomboyish and prefers masculine pronouns, and together, they go through a journey full of doubt and self-discovery.

Wandering Son has been applauded as a coming of age story that treats its main characters with respect and gentleness. Shuuichi, Yoshino, and their older friends are real people with real struggles. Wandering Son subverts the viewers’ expectations, no matter where they stand on these issues, and introduces a complexity that we don’t see in many shows.

Revolutionary Girl Utena is an anime from the 1990s with cult status and devoted fans. Its cult status is almost equivalent to Neon Genesis Evangelion from the same era. So, it rightfully belongs on the top of this list. Galant Utena Tenjou swears to become a prince herself after a mysterious prince comforts her in her childhood when she loses her parents. The only thing Utena has from him is a ring with a rose crest. After she gets some clues that she could reunite with the prince at Ootori Academy, she joins the prestigious school. There, Utena gets involved in the secret sword duels for the hand of Anthy Himemiya, the Rose Bride. What starts as a school-life show with weekly duels evolves into an experience that makes one question everything they know about anime genres, storytelling, gender, and sexuality.

Without Revolutionary Girl Utena we wouldn’t have many of the anime that belong to this list, like Kino’s Journey or Wandering Son. It paved the way for the depiction of gender non-conforming characters and didn’t shy away from showing complex relationships, and breaking apart the tropes of shoujo narratives by questioning the usual tropes. Anthy might not be as helpless as she seems, Akio is a princess charming straight out of nightmares, and Utena is forced to be honest with herself: What does it mean to embody an ideal, to become a heroic prince?

If you want to dig deeper, there seems to be a lineage of cross-dressing women who are excellent sword fighters. Utena’s predecessors are the Rose of Versailles, and if you dig even deeper, Osamu Tezuka’s Princess Knight, a princess raised as a prince with trademark Astro Boy-like eyes.