4. George Bernard Shaw
Dublin, County Dublin
George Bernard Shaw dressed like the eccentric genius that he was. As the only man to win both a Nobel Prize in Literature and an Oscar, Shaw's greatest accomplishment might be trying out surfing at the age of 75. The writer's scraggly facial hair teetered on the line between untamed and gentlemanly, and Shaw definitely crossed this goal off his style bucket list. It was a perfect contrast to his otherwise impeccable suiting.