2. Jay-Z

Occupation: Rapper

Before you start with the “Jay-Z” isn’t stylish rant, just remember: style is more than just about clothes and money (although, those two things are important). It’s about more than just looking cool, too. It’s a whole attitude and way of life, and that’s why Hov is sitting pretty as the runner-up on this list. His resume of hit records and business ventures make him more than just one of the greatest rappers alive — he’s an icon. 

Kanye helped Jay up his high-fashion game with the Givenchy-dipped Watch the Throne Tour, but before that he enshrined hip-hop style staples like the Yankee fitted cap, wheat Timberlands, and white tees. But his style game runs deeper — name an emcee who can wear a suit better.