Cross-dressing is just breaking norms that are arbitrary.
Dressing like a child for a date borders on age play and is a bit...
This is actually interesting. School uniforms are created to communicate that the individual goes to certain school, and even more so, the standart uniforms are made from a combo of formalwear and military uniform - also status signifiers and very much adult.
Usually children resent the uniforms, which are enforced on them strictly to other them from the regular people - obviously there's not much use for the *-schoolers to sit 6 hours looking at people dressed like them.
Gendered clothing exists to communicate the gender of the wearer, to, combining with tastes, identify from for away whether you should approach a person with this-and-that. Of course it's bullshit but even now it's fairly useful in that sense: a person trying to signify their gender usually has a concept of things that are gender-appropriate - it's a self-fulfilling prophecy for a lot of the folk.
Now, why school uniforms aren't considered arbitrary?
To be clear, I still consider deliberately dressing as a child in poor taste, but that certainly isn't the angle I'd go for.
