2. The Fonz
Show (Air Dates): Happy Days (1974-1984)
Actor: Henry Winkler
A leather jacket doesn't get much cooler than when it was hanging around the shoulders of Arthur "Fonzie" Fonzarelli in the decade-long sitcom Happy Days. Just...whoa. His signature greaser style consisted of the aforementioned jacket, a white or black crew-neck tee, jeans, and a mini-pompadour 'do. Then and always, two thumbs up.