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Why bother with such a useless thing as stylish clothing when you have everything you want already? Wearing something you feel comfortable in makes much more sense in this scenario than wearing something you look good in.
I guess that depends a lot on the person. I feel most comfortable when I look good in what I'm wearing. Even if it's just a T-shirt and jeans, it needs to fit right and compliment my appearance. Most of his clothes look disheveled, and ill-fitting, so I guess he just didn't care.
Of course it depends. I don't really care how I look, because no matter what I wear I'm still no Brad Pitt. Quite the opposite tbh. So I strongly prefer casual and comfortable clothes whenever possible. And I don't really care if one part fits the other. The only exception is I don't wear red trousers when I already have red t-shirt... lol
Well, at least you've got that awareness!
Yay!