Lol, I learned to think about why some kids that grow up with that look dress like that. Like on the first page of this topic, it's with the fact that everyone dresses according to their occupation, how they live, etc.
Huge t-shirts with baggy pants, things like that, I started realizing that it usually comes to, (not going to stereotype), kids with a low salary family. It has to do with buying clothes a couple sizes bigger because the person wearing it will eventually grow bigger but still be able to wear those same clothes. Some people might get attached to that style and clothe themselves like that for the rest of their lives, or just do that to look intimidating.
Plus, it's WAY more convenient to go to the restroom with your boxers at the ready.