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Friday Fashion Face-off: Worst-Dressed at the 2021 U.S. Open

Late again. But to make it up to you, we have two polls!

A couple of people suggested Naomi Osaka for inclusion on this week’s worst-dressed list, and while I can’t disagree, I also can’t pile on the poor girl. She’s clearly having a rough time adjusting to the expectations that come with being a champion. My heart went out to her when she was crying in her interview after her third-round loss.

So to demonstrate our compassion, let’s pile on other people and see if we can make them cry instead.

Nominee #1: Evgeny Donskoy

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Believe it or not, this was the best photo of the Russian player available on Getty, which got me to wondering: Which is more depressing—to land on a blog’s worst-dressed list or to make so little impact in a tournament that you merit only four images on Getty?

I’m not a fan of red shorts, and pairing them with a matching red shirt doesn’t improve matters. Actually, now that I think about it, Donskoy’s probably relieved there’s scant evidence of him in this Babolat getup.

Nominee #2: Ugo Humbert

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There’s an older gentleman in my neighborhood who takes his morning constitutional in the same outfit every day. Off-white trousers, light tan checked button-down, off-white newsboy cap squarely on his head. He’s very cute, puttering along with his small determined steps, but he always looks like he’s been dredged in unbleached flour.

If he played tennis, no doubt he’d opt for this beige-on-beige combo by Wilson. (Have you ever wondered why Wilson isn’t a bigger player in tennis apparel? Wonder no more.)

Nominee #3: Diego Schwartzman

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You know how Tennis Warehouse is always out of the color sneakers you want? Almost invariably, when I go to buy, the only shoes left are maroon with purple stripes. If, by chance, there are any shoes in a normal color left, they’re available only in size 2 or 14EEE.

I mention that by way of explaining why my tennis buddy Lori showed up on court recently with these atrocities tied on her feet:

Adidas calls these shoes “Ubersonic Citified.” (I’m no fashion expert, but I believe “citified” is industry jargon for making clothes too ugly to be stolen.)

Up until this week, I was confident Lori owned the world’s most heinous tennis shoes, but it turns out Fila’s also jumping on the fugly footwear bandwagon. Schwartzman looks like he puked Yoo-hoo all over his shoes. And what’s with the random I-really-need-to-do-laundry outfit? (Hey, I’ve been there with the laundry problem. I’d say “no judgment,” but what else is this column but judging, even if hypocritically?)

So there you have it—tennis’s final fashion fiascos of 2021. Thank you to all the tennis sportswear brands for consistently providing fodder for everyone’s favorite face-off.

And MANY thanks to Lori for being such a good sport!!!

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