Sitcom: Seinfeld (1990-1998)
Portrayed by: Jason Alexander 

The thing about George Costanza is that he was dedicated to menswear basics. So it's really funny that, what was just regular guy style in the '90s, turned into a new wave of menswear clothes today. He wasn't afraid to rock a Yankees cap with anything, he wore parkas over plaid shirts on the regular, and knew how to wear a cardigan with ease. Nike Waffle Racers with khakis and a windbreaker? He sonned you.

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