There's a lot to love about Kuragehime, mainly its honesty about who people fundamentally are. It's been said that everybody is a geek of some description, with things like sports and relationships having obsessive fanbases so huge as to dictate what 'mainstream society' is to everybody else. In view of this, Kuragehime depicts Kuranosuke (the cross-dressing guy) as a fashion geek more than anything else, which makes him really endearing. Also, in one episode where he gives everybody makeovers, he does not do so to this one overweight lady in a kimono--wonderfully not because 'LOL SHE'S FAT AND YOU CAN'T FIX THAT WITH MAKEOVERS', but because her personal style is 'very traditional Japanese woman', not 'frumpy slob', and that's not really a problem for his immediate purpose of making this group look presentable in a formal setting.
Anyway, what I realised while watching this, and more fully to-day, was that I'd actually consider dating a girly enough guy as long as it was made clear that the relationship would not be sexual and if we were dating I'd prefer he not have sex with other people. And I'm...really not sure what this says about me, actually!