Age: 20 

Chicago may be home to another stylish celebrity—Mr. Kanye West himself—but  Chance the rapper is proving he's on track to also dominate style. He's a fan of streetwear and isn't afraid to wear prints and patterns, sometimes even mixing and matching the two. What's most notable about his style, though, is that he never really looks like he's trying too hard. More often than not, he just looks like he threw on whatever was clean.