There have obviously been some fashion missteps in the past 500 years in the sport of tennis. Henry VIII pushed for “tall stockings” and “breeches” a la Shakespeare, and the first tennis shoe was a “croquet sandal” made of canvas and rubber sole. However, there are some glaring moments that proved fleeting like animal prints, unitards and flashy underwear, but it seems that there are still a couple classic bits that still make the grade. Bjorn Borgs classic headband is so Royal Tanenbaums it kinda works as a club kid look, and our favorite is Arthur Ashe with the black-rimmed glasses and short shorts. What’s best is that he was most definitely obvlious to his hipster status, which makes it neither ironic nor calculated… just cool. As with most sports, in tennis it’s not about an obnoxiously monogrammed suit, it’s the classics that endure. If that’s what passes at Wimbledon, can’t wait to see what the US Open serves up.

via New York