24. Richard Chai

Occupation: Designer, Richard Chai

Cutting his teeth under designer Marc Jacobs, Richard Chai's eponymous label is known for successfully balancing the line between high-fashion, streetwear, and casual shit normal dudes would rock on the regular. That's actually an apt way to describe his own sense of personal style: a grunge sensibility that's been perfectly tailored, yet kept purposefully unkempt.