21. Dennis Wilson
Band: Beach Boys; Four-Speeds; Dennis Wilson
After spending their first years dressing like a barbershop quartet, Dennis Wilson emerged as the most stylish of the group that championed surfing, girls, and wavy vibes. Whether he was draped in breezy Hawaiian shirts or decked out in advanced '70s gear that not even A$AP Rocky could pull off, Dennis dressed like the lifestyle that he championed while drumming and singing for the Beach Boys. With his relaxed steez and that bears, Dennis wouldn't look out of place in current day Williamsburg or Silverlake.