Sports is all about the W. Win close, win ugly, whatever, just win. But there's a special place in sporting lore for winning with style—many of the greatest athletes, coaches, and reporters have remained cultural icons thanks to the fashion choices that they've made. Athletics can be as much a stage for chambray, fur, and houndstooth as they are for blood, sweat, and tears. And while we're not going to suggest that the pieces outduel the performance, they can take on a status of their own. From a wrestling mask with a 50-year career, to the fedora behind America's team, to a quintet of baggy shorts that scared America in the '90s, these are the 25 most iconic fashion pieces in sports history.

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