There is NO reason why these pants should not be pulled up over his ass. Not only do they fit (they are tight on his calves) but they also have two fail safes to keep them from falling: elastic and a drawstring waist!
If I saw someone dressed like this on the street, I would be like, “Get a job, junkie.” If I saw someone dressed like this on the subway, I would be like, “Don’t look at me, sicko.” But I’d say both these things in my head, because it’s New York and I’m not trying to get killed by a druggie pervert.
Anyway, I think this kid has become so rich that he’s lost perspective on how homeless he’s coming across.