12. Martina Hingis, 2001
There’s really no occasion when a person would need a shirt with one short sleeve and one long sleeve. Apparently Hingis didn’t get the memo.
11. Bethanie Mattek, 2006
Mattek, now Mattek-Sands, is one of the most inventive dressers in women’s tennis. Unfortunately, when her outfits go wrong, they go very wrong.
These socks, for example, look like something your grandma might hand-knit you for your birthday. Most people hide those kinds of things in the back of their closet. Mattek chose to wear them on one of the biggest stages in tennis, the US Open.
10. Andre Agassi, 1992
He might have been the closest thing that tennis had to a rock star at the time, but Agassi still should have thought twice before wearing denim and bright red compression shorts.
Honorable mention in the ugly denim category: Serena Williams in 2004.
5. Anne White, 1985
White took Wimbledon’s all-white rule very seriously, covering her entire body in this lycra bodysuit. It was so controversial that when her match was suspended due to darkness, officials told her she had to return the next day in something more appropriate. She did, but lost the match anyway.
Honorable mention in the ugly bodysuits category: Serena Williams in hot pink.
2. Bethanie Mattek-Sands, 2010
When your outfit was designed by someone who also works for Lady Gaga, maybe you should get a second opinion before wearing it on court.
She also wore this dress to that year’s pre-Wimbledon party. That’s a lot of wasted tennis balls.
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