18. Bjorn Borg's Fila Headband
Famed Appearance: Grand Slam Finals versus John McEnroe
Both Bjorn Borg and John McEnroe had a way with style, seemingly embodying everything that made the 1980's a curious fashion era. When the two met in the 1980 U.S. Open Final, Borg sported his classic Fila Headband, which corralled his locks that seemed to go on for days. While he'd go on to lose the match, he'd prove to win the fashion war against his nemesis. His athletic silhouette will certainly be one we won't soon forget.