Estimated read time3 min read

The last time I was walking through the USTA Billie Jean King Tennis Center—among a sea of tennis skirts, sundresses, and baseball caps, mind you—I saw a woman wearing an ensemble that I could only describe as “cool fashion girl.” There she was, in an oversized rainbow tie-dye T-shirt, long red culottes (or were they cropped cargo pants?), and Tory Burch Pierced Mules—the “if you know, you know” type of shoe my fashion editor eyes clocked in an instant. Naturally, she also had a very chic bob haircut to go with. Anyway, when I think about what to wear to the US Open, I think about this woman. I hope she’s living her best-dressed life as I type this.

Though tried-and-true tennis pleats and courtside whites will always be in style for a Grand Slam tournament, I’m keen on switching up my sartorial choices for the New York-based tennis tournament this year. More cool and less prep, if you will. If you’re with me, see the outfits I’m predicting cool girls in the know will be wearing this season. I can already picture these ready to watch stress-inducing rallies and jaw-dropping aces, all with a Honey Deuce in hand.

Effortlessly Cool

Inspired by the aforementioned woman who got me started on this journey, I present to you my version of this look, complete with a tie-dye T-shirt, extra-long and loose shorts, and, of course, the easy leather mules that were made for grabbing someone’s attention.

Zewel Tie-Dye Logo T-ShirtIsabel Marant Étoile Zewel Tie-Dye Logo T-Shirt

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Credit: NordstromMeldert Bermuda ShortThe Frankie Shop Meldert Bermuda ShortCredit: The Frankie ShopPierced MuleTory Burch Pierced MuleCredit: Saks Fifth AvenueRizzo 60mm Navigator SunglassesBarton Perreira Rizzo 60mm Navigator SunglassesGossip Small Shoulder BagGucci Gossip Small Shoulder BagCredit: GucciThe Fashion-Forward Track Set

Now seems like the perfect time to lean into a polished athletics-inspired set, no? Personally, I see the windbreaker as one of the It pieces to have for this year’s summer-to-fall transition, and with the matching shorts, it might not more chic (or comfortable) than that. Dress it up with a pair of wedge sandals, simple jewelry, and a cute raffia bag for your day.

The Tennis WindbreakerFrame The Tennis WindbreakerCredit: FrameThe Tennis Athletic ShortFrame The Tennis Athletic ShortCredit: FrameVinnie Wedge Thong Sandal 50Stuart Weitzman Vinnie Wedge Thong Sandal 50Credit: Stuart WeitzmanBetween HoopsMejuri Between HoopsCredit: MejuriTsubi RaffiaPolène Tsubi RaffiaCredit: PolèneCool Girl Prep

If you’re going to embrace the theme, you might as well do it in a fresh way, right? Right. Here, I’ve pulled together a Miu Miu-esque ensemble with a classic polo shirt, a khaki cargo skirt, and the current New Balance sneakers I personally swear by. Oh, and how cute is that mini duffel bag from the Sandy Liang x Porter collaboration? That itself will give you cool-girl status in an instant.

Essex PoloWilson Essex PoloCredit: WilsonEmery SkirtMalbon Emery SkirtCredit: Malbon204L SneakerNew Balance 204L SneakerCredit: NordstromPony Chino Baseball CapPolo Ralph Lauren Pony Chino Baseball CapCredit: Bloomingdale’sLoaf BagSandy Liang x Porter Loaf BagCredit: Sandy LiangThe Breezy Shift Dress

While I’m personally not one to wear a dress to a sporting event, it’s not out of the question—and especially not for the US Open! But instead of embracing a tennis dress or a polo mini, consider a chic shift dress that will work well beyond the stadium grounds. I love the idea of sporting it with a bandana, and then giving it a bit of borrowed-from-the-boys grit with leather loafers and red ankle socks.

Mini Shift DressSmythe Mini Shift DressCredit: SmytheKirsten BandanaThe Garment Kirsten BandanaKatherine LoaferLarroudé Katherine Loafer

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Credit: LarroudeAgnelli SockComme Si Agnelli SockCredit: Comme SiIcons Acetate Rectangle SunglassesLacoste Icons Acetate Rectangle SunglassesCredit: LacosteOff-Duty Athleisure

I wore a version of this look the other day while running around the city, and I fell in love with the pop of fuchsia against the muted blue tone of the button-down shirt. It doesn’t get more fashion-girl-off-duty than a button-down with athletic shorts and Birkenstocks, which makes it a perfect ensemble for a day of Honey Deuces.

The BoyfriendWith Nothing Underneath The BoyfriendCredit: With Nothing UnderneathNylon Taffeta ShortsLos Angeles Apparel Nylon Taffeta ShortsCredit: Los Angeles ApparelArizona Rivets Slide SandalsBirkenstock Arizona Rivets Slide SandalsCredit: Bloomingdale’s1998 Montauk Small ToteJ.Crew 1998 Montauk Small ToteCredit: J.CrewDele SunglassesWhy Trust ELLE

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