 If you liked
Paradise Kiss
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 ...then you might like
Kuragehime
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Anime adaptations of josei manga with an emphasis on fashion. One would assume this means most males should run far away with their anuses clenched and never look back, but no: they are strangely accessible and appealing even to the more manly males that frequent this site, such as myself. Seeing adult(ish) characters mentally dealing with the highs and lows of AN ACTUAL SEXUAL RELATIONSHIP IN ANIME!!111! is appealing in Paradise Kiss. Princess Jellyfish's fujoshi-in-a-boarding house freakout gag humour makes it more of a comedy than a drama and even more male-accessible as a consequence. And the fashion aspects are presented from the respective heroine's
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Recommended by AironicallyHuman
Those shows are both romances (to some degree) about girls that changing their appearance end up changing their whole life. Fashion is also of importance in both series, we deal with models and designers, though in ParaKiss the main heroine is a model and in Kuragehime she's a designer (of sorts).
Fashion, cross-dressers, a little romance~ If you enjoyed Paradise Kiss, you'll love Kuragehime. The latter is definitely more humorous! Both's main girl has no knowledge of fashion. Both show the distances from being normal and/or an otaku to becoming stylish and beautiful.
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Recommended by Shadowmancer
Theses are both great anime about fashion and have a shy characters and a very flamboyant one trying there damnedest to make them come out, both times it is a girl who is she and the guy who is out there, In Kuragehime the guy does dress as a girl but ohwell there is one in pardise kiss aswell. Pardise kiss has more romace with the main then Kuragehime but both are great anime and should be watched. Both aired in the same time block known as noitaminA.
Paradise Kiss and Kuragehime are both josei anime, dealing with life in a big city. Both deal with romance issues and both contain cross-dressers. Paradise Kiss is more realistic with a huge amount of fashion, while Kuragehime contains a little bit of fashion, but a huge amount of comedy.
Characters of these 2 are into fashion and go into detail about Japanese fashion and culture.
Dress designing. Cross-dressing. Josei. Small, but colourful cast.
Paradise Kiss is mostly serious and realistic, while Kuragehime is more humor based.
These are the most fashionable animes out there!!? .ﾟ☆(ノё∀ё)ノ☆ﾟ.
They are also the only animes I've ever found where they are sewing a lot. As a fashion nerd and a cosplayer I can't tell you enough how happy it makes me to watch anime characters work together to sew something!! (o✪‿✪o)
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Recommended by SwediCandy
Paradise kiss is about a normal highschool girl who has been good all her life until she is scouted by a group of fashion designers called "ParaKiss" its similar to Princess Jellyfish in many ways and is also made by Josei like Princess Jellyfish.
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Recommended by AnimeParadise
You know what the anime world needs more of... fashion! There is a short supply of anime that focus on the more fabulous side of life, and even more so a female adult targeted audience(not to say these shows can't be enjoyed by everyone), both shows carry a more adult feel while still keeping their innocence and comedic sides.
These shows display more mature relationship without turning to an ecchi route. While both showcasing great style and strong friendships.
This one is more lighthearted and not really as much drama as in nana but it also has a similar vibe I would say. The main characters are cute and nice, also some fashion related things here aswell.
Both are fashion related in a way, where they show a whole new "fashion world" to the protagonist, opening their eyes to what they truly want. Paradise Kiss being more mature.
Both have VERY similar vibes and stories, both are about the fashion world and outcast girls.
Both have aspects of fashion and people who are seemingly different forming beautiful relationships. Both also touch some sensitive topics quite well and maturely. I'd also suggest Kuragehime if you liked Nana :)