Show: Clueless

Long before he was scrub buddies with Zach Braff, Donald Faison was remembered as Murray in Clueless. His character was dating Stacey Dash, so he didn't have it that bad. He was also the best-dressed male on that show. And when girls like Cher and Dion are killing it in designers like Azzedine Alaia, you know he had to come correct. His streetwear-inspired legacy still lives on.