I guess its just more of the cutting of girls clothes makes it look awkward on guys but really it shouldn't matter, clothes are clothes, they just represent who people are and if they want to express it in that way it should be fine, i think its just mainly media and stuff that is going against it a lot
It's about being masculine or feminine, a woman can be masculine in ways because it means she's strong, athletic. But if a man chooses to be feminine, he just seems weaker, men are in general naturally stronger than women. And women are naturally more caring than men. A woman can be stronger than average, and still be caring, but a man who is weaker, won't become as good as women at being caring. It throws the mechanism out of whack basically.
A weaker man, is a less able man, less dependable, especially if they have to be treated like women, who are generally more emotional.
Women's clothing looks weird on guys. I can ask why is it ok for girls to date good looking guys 9 times out of 10 and no one questions her? But if a guy only dated hot girls he's only interested in sex, Or why is it OK for women to date rich guys but not ok for guys to date girls for their bodies?
There are things which you'll never be able to explain. It's like why don't we want to have sex with dumb people if we're not gonna have stupid kids from them anyways? Just because . And no, I don't think that he should be wearing skirts to school. It's just embarrassing.