32. John Daly's outfits are a walking punchline.
When: 1991 - Present
John Daly may have won several battles in his life, but he's definitely lost the sartorial war. Yes, golf is a chance for old white men to dress like Yalies on acid, but Daly manages to continuously take it too damn far. There's a very wide, argyle-patterned line between acceptably outrageous golf attire and what Daly does, and it's pretty clear which side he falls on.