"There is a boy who wears Lolita at my school, but like, the girl version of Lolita. Isn’t that weird?"
I do not know if this is a statement or a question, but no, that is not weird at all. Everyone can express themselves how they see fit.
These guys are usually lovingly referred to as brolitas. They are very much welcomed in our community and I think it is awesome that he has the courage to wear what he wants to school. I would think it would involve more backlash and rude comments from others than a girl wearing Lolita fashion.