September’s Tunnel ‘Fits we can’t stop thinking about
From the US Open courts to New York Fashion Week runways, athletes served up effortless transitional looks throughout the month
Between the US Open and fashion month kicking off with New York Fashion Week, September brought daring ensembles and effortless appeal. Some of our favorites delivered multiple A-plus looks, making it easier said than done to select just one.
Scroll down to see who nailed the transitional summer-to-fall looks the best. With the NFL kicking off, the NBA returning, the WNBA playoffs underway and fashion month wrapping up, circle back next month to see who makes a fourth-quarter push for the year’s best-dressed athlete.
Malik Nabers
Malik Nabers kicked off his third season as a New York Giant in a burgundy leather jacket, dress shorts and matching shoes. Opting for tailored shorts instead of pants keeps the look casual, but if this is how he’s starting off, we’re in for four more months of head-turning outfits.
Skylar Diggins
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Even in all black, Skylar Diggins still gives us detail and drama. The Chicago Sky star stepped out during New York Fashion Week in a Simkhai look from the brand’s Fall 2026 collection. Styled by Sydnee Paige, the Orvik leather jacket with sweeping cape sleeves was paired with the coordinating Corrine leather pants, featuring a relaxed straight-leg silhouette and adjustable drawcord hems.
Serge Ibaka
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As one of the hottest presentations of New York Fashion Week, the KidSuper runway show boasted a star-studded crowd and even featured a performance by Ms. Lauryn Hill. Arriving in a patchwork long jacket that’s so distinctly KidSuper, NBA champion Serge Ibaka paired it with terracotta slacks, black shoes and a cap, letting the statement piece take center stage while the muted tones underneath gave it room to do all the talking.
Trinity Rodman
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After every Ben Shelton victory at this year’s US Open, the camera panned to his girlfriend, Trinity Rodman, whose proud grin became one of the tournament’s most feel-good sights. For Shelton’s five-set thriller against Carlos Alcaraz, Rodman leaned into a preppy look, sporting a slightly oversized Adidas Originals track jacket with a flirty miniskirt, Chanel handbag and Adidas sneakers. The bright orange beret provided an unexpected finishing touch.
Serena Williams
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Serena Williams’ return to the US Open was spoiled by an early exit in doubles, but that didn’t stop the tennis great from enjoying New York City. For Net-a-Porter’s “Incredible Women” party, Williams wore a bright purple Loewe minidress with a delicate fringe for added whimsy, pairing the look with black pumps to keep the ensemble polished.
Tari Eason
Nailing the sleek and minimal look, Houston Rockets forward Tari Eason wore an oversized double-breasted blazer in muted olive-charcoal hues layered over a simple white tank for Vivet’s NYFW debut. Black wide-leg trousers and loafers complete the look, proving even a baggy silhouette can still look flawless.
Azzi Fudd
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The People’s Princess brought her signature mix of sporty and cool-girl style to Coach’s NYFW show, arriving head-to-toe in a fit from the brand’s Fall 2026 collection. Fudd layered a striped wool varsity jacket over a satin pinstripe button-up and leather bralette, then kept things relaxed with loose-leg denim and finished the look with Coach accessories and rectangular shades.
Jarred Vanderbilt
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Los Angeles Lakers forward Jarred Vanderbilt brought a little old school drip to Vivet’s NYFW show, captured outside Cipriani in a burgundy leather jacket, crisp white henley, and loose grey trousers. Black loafers, a gold chain link belt and layered jewelry added polish, but that navy Yankees cap was the real finishing touch. A quintessential New York staple that made the whole look feel right at home.
Jordan Chiles
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Styled by Jason Rembert, the decorated Olympic gymnast brought old Hollywood glamour to Christian Cowan’s NYFW show in a sharply tailored black blazer minidress, cinched at the waist for a sleek, sculpted cut. The oversized brown faux fur framing the neckline and spilling onto the cuffs was a fun contrast against the structured dress. Complete with black pumps, this feels perfectly at home in Cowan’s world.
Simone Biles
For a night with Audemars Piguet to celebrate the launch of the Royal Oak “Serena Williams” Limited Edition line, Biles stepped in a sculptural asymmetrical hemmed dress. Nude satin peep-toe pumps matched the color scheme, and a nude-strap watch tied back to the evening’s occasion.
Lewis Hamilton
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Lewis Hamilton made quite the entrance to Monza, arriving at Ferrari’s home race behind the wheel of his newly restored Ferrari F40. The seven-time world champion wore a Saint Laurent Fall 2026 double-breasted suit with a white shirt, black tie, and camel overcoat, finishing it off with a Kangol Tropic 504 beret. 10’s 10’s 10’s all across the board.
Sydney Colson
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Syd Colson made her NYFW runway debut in Keem Studios, strutting in a rich brown short-suit with a white tank underneath. Apparently, Colson liked the look so much she put it right back on the next morning to film her podcast, Unsupervised. Now that’s an outfit worth repeating.
Angel Reese
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The ATL Barbie was giving full Gucci ahead of the Atlanta Dream’s matchup against her old team, the Chicago Sky, arriving in a monogrammed Gucci pencil skirt paired with a fitted light blue crewneck tee. She kept the accessories in the family with a Gucci belt, brown-and-gold heels, layered gold jewelry, and a Gucci necklace. Another tunnel fit that proves Reese never misses.