14. Jim McMahon's Rozelle Headband

Debuted: 1986
Famed Appearance: On the field for the Chicago Bears in 1986

For those of you unfamiliar, “he's the punky QB known as McMahon, when he hits the turf he has no plan.” Jim McMahon exuded style on and off the field, but his lasting memory will be the headband he wore with the name “Rozelle” scrawled across it, a not so subtle jab at the commissioner at the time, who had fined McMahon previously for having a corporate sponsorship (adidas) on a previous piece of headwear. Bear down.