19. George Costanza
Show (Air Dates): Seinfeld (1990-1998)
Actor: Jason Alexander
Unlike title character Jerry Seinfeld, his faithful sidekick George doesn't indulge in too many '90s fashion trends. In retrospect, thank God. Instead, George sticks with classic pieces, including plaid button-ups, navy and forest-green anoraks, bright polos, crisp Oxford shirts, and khakis. Besides a few awfully patterned ties and the odd ill-fitting jeans, his style choices have admirably stood the test of time.