Show (Air Dates): Gilligan's Island (1964-1967)
Actor: Jim Backus

Shipwrecked but still dapper on the daily, Gilligan's Island's Thurston Howell III didn't let a little island heat stop him from dressing in a monogrammed jacket, button-up, sailor cap, and ascot. Take heed the next time you're about to lose all dignity and don flip-flops and a tank in public.