Borough: Brooklyn (Bed-Stuy)
Signature style: Brands you dream of affording, clothing designed by his friends, and a suit-and-tie. 

The true sign of a stylish individual is their sphere of influence. It seems like a lifetime ago when Jay-Z expressed his distaste for jerseys and over-sized fashion in favor of raw denim and a button-up shirt. But Jay unknowingly helped introduce the possibility of rappers dressing like adults.

Since the lyrics on 2003's "Change Clothes," Hova has since become a style chameleon—rocking the most expensive of kicks, gear everyone can afford, and dressing like Frank Sinatra when the time calls for it. The Brooklyn native has already cemented his spot in hip-hop history, but when you're best buds with Kanye West, married to Beyoncé, and consistently sit courtside at NBA games, it's hard not be one of the best-dressed rappers, now.