10. Yasiin Bey
Height of Style: 2009 Ecstatic Tour
Signature Look: Tailored suits, five-panel caps, hardbottoms, accessories
When he first came on the scene, Dante Smith looked like most other backpack rappers. And as the MC formerly known as Mos Def's art form evolved, so did his sartorial style. It was around 2009 when he consciously decided to start wearing a suit and tie every day. Ranking Paul Smith, Caminando, and Isaia as some of his favorite labels, it was NYC brand Ale et Ange that really spoke to him. Admiring the way the designers mix hip-hop inspiration with modern fits and crisply tailored clothing, he's admitted that the brand makes up a majority of his wardrobe today. If anyone could talk about style with Kanye without getting embarrassed, it's definitely Mr. Bey.