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.
25. Manny Ramirez's Baggy Pants/Do-Rag Combo
Debuted: 2001
Famed Appearance: Patrolling left field for the Red Sox
The ethos, “Manny being Manny” certainly spilled over into the fashion world for the Dominican slugger. Working from the top down, Manny's do-rag became synonymous with his dreadlocks, something that would get him in hot water with Joe Torre in L.A. And from the bottom, Manny was known for sporting baseball pants that looked more suited for an MC Hammer video. If skinny jeans are any indication as for what's to come for baseball uniforms, Ramirez got out just in time.