The Most Stylish Chicago Rappers Right Now

5. Sir Michael Rocks

A style maverick.

Neighborhood: Matteson

Back when the Cool Kids were jamming, their ode to the early 90's look was undeniable. From fat gold chains with classic NBA jerseys to acid wash jeans. Mikey definitely helped bring that retro style back, and he's never looked like any other rapper out with amix of high-end designer, retro fashion mash-up that's all his.

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