50. Bill Cunningham
Occupation: Photographer, The New York Times
Signature style: Blue-Collar Awesomeness
Notable work: On The Street, his weekly NYT street-style roundup.
Bill Cunningham makes this list because style isn't about fashion trends or designer labels, it's about making your clothes work for you. His iconic French blue chore coat has been his uniform for a long time now, and the khaki pants and plain black shoes he pairs them with are a testament to how you can mix one statement piece with more conservative clothing for a reliable uniform.