Like I said, he wants people to know he likes a certain way of life (hip hop) and it may help with immediate contact for likeminded individuals, rather than if he dressed like a businessman or a polo player. I honestly don't see anything wrong with that except for the fact that (ahem) some of you have a pre-conceived notion that just because one dresses like a typical rapper that they must be losers just because they're not big name rappers themselves.
Most young men today are losers---they've "lost" the battle in defining themselves. It's funny how you can spot the real "thugs", Gs, playas, vs the fake ones...the fake ones have to go all out to the extremes (like this guy)...I remember seeing white dudes wearing du-rags, and not knowing what they were really for...to keep the waves in, some would ask me wear mine was and would ask wear they could find diff colors (I had, black, blue, light blue)---American suburbia is entranced with Hip-hop culture, the hardness, but they romanticized that, but don't want the downside...shootings, stabbings, the living conditions.
Most dudes who are into hip hop, don't dress like that, at least the ones I'm around (Balt-Wash), people who tend to dress like that, may like hip hop---but they are more into the imagery...and what is sad, is this dude can later on dress up in a suit and tie and claim, "this was a former lifestyle, a fad", whereas someone "else" will still have that stigma attached to them.