Michael Jordan
Credit: Craig Jones / Getty Images

Michael Jordan is a style icon – and not just because of his Air Jordan sneakers. He started the trend of wearing baggy shorts in NBA games. Looser-fitting shorts accommodated his University of North Carolina shorts, which he always wore underneath his Bulls uniform. Six championships may have added more to Jordan's legacy, but the shorts have an important place in Jordan lore. He wanted to win so badly that he wore tokens of past successes into battle.