You know we had to put our dude Russell near the top of this list. Our NBA cover star was instrumental in making people pay attention to basketball players' style off the floor. Most people may have poked fun at his bold prints and geek-chic steez, but we stylish few knew that Westbrook was headed in the right direction. His penchant for taking style risks may have earned him a few critics, but not giving a fuck about the haters is a crucial step in earning your badge as a style icon.