How come a girl can wear guys clothes and look cute or wear a suit and look hot, but when a guy wears a dress or a skirt it’s weird?
because our society thinks it’s degrading to be feminine
To be more specific:
If a girl dresses as a guy, she’s taking on masculine traits. This is seen as a step up for her.
If a guy dresses as a girl, he’s becomming feminine, which is seen as a step down. It seems weird the same way it would seem weird to see Bill Gates in a wife-beater and jeans (since formal attire is seen as a step up from casual clothes).
This is the same reason boys are mocked for crying and cheer-leading, while girls are celebrated for fighting and playing rough sports.