22. Payne Stewart's U.S. Open Ensemble

Debuted: 1991
Famed Appearance: On the Hazeltine National Golf Course in 1991

Payne Stewart's untimely death not only deprived sports fans of one of the more skilled and personable players on the tour, but it also ended an entertaining run of golf ensembles that Stewart would wear at various tournaments across the United States. One of his most memorable was the navy blue and orange striped get-up, paired with his signature cap, which he wore when we took home the top prize at the 1991 U.S. Open. A little silly looking? Of course. Golf could use a few doses of silly though, word to Billy Madison.