The story of Kuragehime (2014) takes a look into the apartment complex of five unmarried women who can be classified as otaku, unsociable adults with obsessive interests who are typically shunned by society. These women, including the main heroine Tsukimi, are all designed to be conventionally unattractive. They are considered, and even consider themselves, to be an entirely different species from the upper-class beauties known as the Stylish.
However, one day, Tsukimi has a fateful encounter with one of the Stylish-- a stunning "woman" who, on a whim, comes to her aid in a social situation. It isn't until after the stranger stays the night in her room and removes his flowing wig that it is revealed to be Kuranosuke Koibuchi, the son of a powerful politician who just happens to be very interested in fashion and cross-dressing. Under the alias "Kurako," he continues using his feminine persona to help himself as well as his new friends. Through his genderbending, Kuranosuke stands as a strong testament to his own ideal about the transformative power of fashion to influence how a person is perceived.
Upon their first meeting, Tsukimi describes Kuranosuke as "wide-eyed, fair-skinned, with long slender limbs," an image that she instantly recognizes as beautiful. Ironically, this pale slenderness is Tsukimi's image of beauty mostly because it reminds her of a jellyfish, which happens to be her obsessive interest as an otaku... but, conveniently, this is a common image of female beauty as well. It's not ideal to limit the view of beauty to this popular standard, but it is funny how Tsukimi reached the conclusion from such a different angle, leaving one to consider what a wide range of traits people might find beauty in for various reasons.
In any case, because he does fit this standard, Kuranosuke's natural androgyny makes it easy for him to believably cross-dress, which he is interested in for several reasons that all have little to do with gender identity itself. In addition to the influence of his deceased mother, who once mused about wanting a daughter, he enjoys exploiting his ability to pose as a girl in order to escape his family's responsibilities and get out of things he doesn't want to do.
Most importantly, he is interested in cross-dressing because he loves fashion, and he likes to be able to test out clothes and make-up on himself. He comes to find that he loves even more to test his transformative talent on those with lesser-recognized beauty, like the otaku, and he truly believes that anyone can be made beautiful with the right clothes and the right style-- that is, with the right frame.
In one very clever scene, Kuranosuke performs makeovers on the five nerdy girls to make them fit in with the rich and glamorous. He spices up the outfits of the first four, but leaves the one old-fashioned doll collector otaku in the kimono she normally wears. The kimono was, up until then, just another eccentricity among the crowd of her eccentric friends, but among a group of stylish people it elicits an image of class and nobility. Thus with no change in appearance, but simply different framing, she appeared more attractive and respectable.
The same subjectivity often applies to the framing of gender. Apart from Tsukimi, the women of the apartment never discover that Kuranosuke is actually a male. As they refer to their circle of friends as the "Amars," or "Nunnery," they take pride in their avoidance of men. Thus, even though Kuranosuke acts no differently in or out of female clothes, simply believing him to be a woman made it more possible for them to allow him into their personal space.
Even so, the assimilation isn't easy. There was still the hurdle of him representing the "Stylish" society whom the otaku resentfully alienate, and with whom their personalities clash. However, this barrier is also somewhat broken, as it comes to light that the Stylish often seem to have oddly specific fixations, not much different from the otaku, and values that overlap more than might be expected.
Kuragehime is a beautiful series that goes to great lengths to demonstrate that beauty is in the eye of the beholder, and the circumstances of the beholding, in a world where so many value judgments get taken for granted.