There are few roles in anime as belittled as that of the crossdresser. Although there are exceptions -- usually girls in men's garb -- who escape mockery, most crossdressers in anime are subject to constant harassment and sometimes outright transphobia.
Princess Jellyfish, released in 2010, is an oft-forgotten anime and a love letter to the oddities and rejects. One of its main characters, Kuranosuke, is an entirely unapologetic socialite crossdresser who stumbles upon Tsukimi, the social recluse main character. As Tsukimi says, Kuranosuke is "A strong, beautiful, manly princess" who uses his self-confidence to prove that crossdressing isn't a joke, but instead part of his persona that can be used to create more compelling stories.
To understand why Kuranosuke is such a refreshing take on the crossdressing trope, it's important to look at how that trope is typically used in anime. Crossdressing here tends to fall into one of three categories: for humor, for plot, or because of actual character preference. The first category is very familiar. A boy dresses as a girl either by choice or through force, which is depicted as amusing either because he is degraded or because other male characters are attracted to him.
This occasionally happens with girls accidentally attracting unwanted romantic intentions, but is largely reserved for boys, as it's seen as more humiliating for a boy to dress as a girl than vice versa. For example, Secret Princess features a male character who is forced to dress as a girl and is then sexualized through panty shots and thoroughly humiliated throughout the entire series.
The second category is when a character cross dresses for plot. For instance, Haruhi has to dress as a boy throughout Ouran High School Host Club in order to pay off her debt, while Strawberry Eggs requires a man to dress as a woman to get a teaching job at an all-girls school.
Lastly, a character may choose to crossdress out of purely personal choice. Mayumi from Pretty Boy Detective Club elects to dress as a boy in order to join a school club. Some of these characters have a genuine desire to pass as a different gender -- Rui from Gatchaman Crowds maintains a firm crossdressing persona while out in public -- while some are perfectly open about their gender, such as Astolfo from Fate or Felix from Re: Zero. It's important to note that some characters in this category are outright or strongly hinted at being transgender, such as Ruka from Steins;Gate, who uses time travel to actually become female at birth. Unfortunately, even crossdressers by choice or transgender characters are not immune to being harassed or being treated as a joke, such as Ruka actually having her skirt lifted.
However, Princess Jellyfish gets crossdressing right, treating characters with respect and not demeaning their personal choices. Kuranosuke falls into the third category of choosing to crossdress, but is also comfortable identifying as male. Where he differs from Astolfo or Felix is his main role in the series and how his crossdressing adds to his character rather than being used as merely an amusing trait.
Princess Jellyfish itself is about a group of social misfit women called the 'Amars' who all live together, banded against men in general and anything that threatens their reclusive lifestyle. Tsukimi is one of the Amars and has a particular fascination with jellyfish. One night, after a failed attempt at going to an aquarium, Tsukimi goes by her favorite pet store, only to discover that the life of her favorite jellyfish has been put in danger. She fails to explain the problem to the male shopkeeper, which is when she runs into Kuranosuke, an intensely stylish man who Tsukimi mistakes as a woman.
Due to this chance encounter, Tsukimi ends up going back to the apartment with both Kuranosuke and a new jellyfish. She allows Kuranosuke to stay the night and only discovers that he was crossdressing when she sees him without a wig. Thus begins the story of Kuranosuke attempting to befriend and help the Amars as they fight to save their apartment building from being torn down.
Kuranosuke chooses to crossdress out of a desire to distance himself from his wealthy and heavily political family, as well as to feel closer to his estranged mother. He is known to be very popular and manages to charm his way into any group of people, even the Amars, who initially distrust his stylish appearance. The only one of the Amars that Kuranosuke chooses to reveal his gender to is Tsukimi, and she respects his desire not to be exposed. Kuranosuke is not mocked for his choices, and neither is he portrayed as perverted or used as an object of humiliation. The misunderstandings between him and the Amars rise solely because of their social differences.
The most turbulence over Kuranosuke's lifestyle comes from his own family. His brother Shū is embarrassed by Kuranosuke's habits and his father is an openly intolerant person, not wanting to even see his son. However, Kuranosuke is never made into a joke, degraded, or forced to crossdress for plot purposes. In fact, Kuranosuke nearly didn't crossdress at all. The manga artist for Princess Jellyfish initially wrote Kuranosuke as a pretty girl, only changing the character when the editor suggested it as a fresh idea. As a crossdressing man, Kuranosuke has the chance to be even more self-assured in his personality; crossdressing was seen as an opportunity to make a character even better -- a positive influence on the story instead of just a trope.
Romance is often denied to anime crossdressers, either because they're side-characters or too busy being the butt of the joke. There are obvious counterexamples -- Haruhi and other mostly female characters -- but the relationship between Kuranosuke and Tsukimi is a slow-paced development between two people who would normally have ever met. Kuranosuke is immediately comfortable with Tsukimi, as shown by him taking off his wig and dress right in front of her, and their relationship over the show becomes one of Kuranosuke realizing he can use his confidence to help Tsukimi see how lovely she truly is. While this begins as purely cosmetic, Kuranosuke soon realizes how talented Tsukimi is when it comes to sewing, and eventually helps her sweep a local fashion show and establish her own brand.
Tsukimi's relationship with Kuranosuke helps her break free of the social misfit label she has imposed upon herself as his self-assuredness begins to rub off. In return, Kuranosuke is able to escape a superficial society and become part of a group of people where fashion and social status don't matter at all.
By the end of the show, Kuranosuke has feelings for Tsukimi, and while the two never explicitly enter a romantic relationship, all signs point in that direction, especially with the feeling of accomplishment and endearment Tsukimi and Kuranosuke share come their successful fashion show. Kuranosuke's feelings of devotion, protection and even jealousy grant him the title of love interest with a degree of complexity rarely shown to crossdressing characters, fleshing him out more as a person rather than a stereotype.
While Princess Jellyfish is not without its issues, when it comes to Kuranosuke and the depiction of crossdressing, this 2010 anime is sadly still leagues ahead of many anime being produced today. Crossdressing is not shown as something to laugh at but rather something to accept as natural for people who desire that. Kuranosuke says it best: "I’m a boy. I just like dressing up in women’s clothes. I’m perfectly normal.” It just might take some time for the world to catch up with him.
