Nick Wooster isn't a household name, but the street style icon has been making waves in certain circles for years.
The gray-haired, tattooed, Crocs-wearer breaks almost all the rules, yet somehow always ends up looking great. We especially appreciate his mixing of traditional preppy styles with his heavily tattooed arms and waxed handlebar mustache.
He's worked with brands from Neiman Marcus to Polo Ralph Lauren, and his influence is just enough to make our sixth spot.