Sitcom: Family Ties (1982-1989)
Portrayed by: Michael J. Fox 

Young Republican Alex P. Keaton kept dressing conservative awesome. We're talking the heyday of prep: penny loafers, oxford shirts, slim but not skinny ties, and straight-leg khakis. He also knew how to dress down without looking like a chump: a navy bomber and a football cap. If more Republicans (ahem, Paul Ryan) started dressing like him, maybe we'd take them a little more seriously.