13. Chief Keef
We actually named Chief Keef one of the most stylish rappers in Chicago right now. But that's because his style (dreads, small polo shirts, and sagging True Religions) has influenced a generation of fans in his hometown. Kids want to look like him, and that's a powerful connection to have.
That's why we think the young rapper should dress better—these kids need to change out of pants that are too small (and way too low), gaudy designer belts, and retro Jordans that real heads bat an eye at. We understand, Keef's been in-and-out of correctional facilities, so he hasn't had a chance to be up on the Interwebs checking out the latest styles, but chilling with the likes of Kanye and Pusha T should inspire him to grab some new threads. And we hope he does.