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The 15 Most Stylish On-Field Athletes of All Time Image via Getty Images / Ron Vesely

15. Rickey Henderson

Sport: Baseball
Years Active: 1979-2003  

Between Dennis Eckersley, Jose Canseco, and Mark McGwire, the 1990 Oakland Athletics were loaded with cocksure, borderline psychotic brutes. But no player personified the unapologetic vanity of that clubhouse like Rickey Henderson. Sporting knee-high stirrups and wraparound shades, this guy patrolled the vast outfield of Oakland Coliseum with the flagrant confidence of a professional wrestler. When stealing a base, Henderson slid headfirst every time in a seemingly concerted effort to wear infield dirt like an accessory, which only made his neon green batting gloves pop even more.

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