If you’ve ever scanned the stands at Arthur Ashe Stadium during a sweltering late-August afternoon, you’ve seen her. It’s basically a law of physics at this point. Amidst the sea of baseball caps, sweaty tourists, and overpriced Honey Deuce cocktails, there sits a woman who looks like she just stepped out of a climate-controlled vault in the 1st Arrondissement.
The Anna Wintour US Open connection isn't just about a celebrity liking sports. Honestly, it’s a full-blown cultural ritual. While other A-listers show up for the finals to be seen, Wintour is there on a random Tuesday morning for a qualifier match. She’s a tennis obsessive. A "tennis stalker," as her friend Baz Luhrmann famously called her.
But there’s a lot more to her presence in Flushing Meadows than just wearing Chanel in the humidity.
The Uniform: Why the Sunglasses Never Come Off
People always ask about the shades. It’s the first thing you notice when the camera pans to her in the President’s Box. She wears those dark, oversized Chanel sunglasses even when the sun is setting or the stadium lights are blinding.
Some think it’s just her "Devil Wears Prada" persona. Others think she’s hiding a nap.
The reality is a bit more human. Anna has often mentioned that the glasses are a shield. They allow her to watch the match—and the crowd—without anyone knowing where she’s looking. It’s about privacy in a very public place. There’s also the fact that they are prescription. In various interviews, including a notable chat with The New Yorker, she’s hinted at her eyes being sensitive. At the 2025 US Open, she was spotted in her signature black frames, pairing them with a rotating collection of floral midi dresses that have become her de facto tournament uniform.
She doesn't do "athleisure." You won't find her in a tracksuit.
Usually, it's a printed dress, maybe a light cardigan draped over the shoulders, and always those Manolo Blahnik slingbacks. It’s a masterclass in staying "on brand" while sitting on a plastic seat for five hours.
It's About the Friendships, Not Just the Forehands
You can tell a lot about Wintour’s standing in the world by who she sits with. Over the years, the Anna Wintour US Open seating chart has been a "who’s who" of power and talent.
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- Roger Federer: This is the big one. Their friendship is legendary. Anna has been a Federer superfan since 2003. She’s flown across the globe to watch him play, and when he retired in 2022, she wrote a deeply personal tribute in Vogue. She famously helped him with his fashion choices, while he, in a hilarious trade-off, tried to help her with her serve.
- Serena Williams: Anna was one of the first people to truly bridge the gap between elite fashion and the Williams sisters. She saw Serena’s potential as a style icon long before the rest of the industry caught up.
- The 2025 Crew: This past year, the guest list in her orbit was wild. She was spotted sitting with Rami Malek and Hugh Jackman. She even hung out with Lewis Hamilton during the women’s final.
It’s a specific kind of networking. In the heat of Queens, deals are made and Met Gala invites are likely discussed between sets.
The "Stalker" Reputation
Anna isn't just a casual fan who knows the big names. She knows the stats. She knows the juniors.
She reportedly wakes up at 5:00 AM every day to play tennis before heading to the Condé Nast offices. That’s commitment. When you see her at the US Open, she isn't checking her phone. She isn't chatting away while a point is in progress. She is locked in.
There’s a misconception that she’s only there for the "scene." If that were true, she’d show up for the trophy presentation and leave. Instead, you’ll see her at the outer courts, watching the up-and-comers. She has a genuine respect for the discipline the sport requires. Tennis is solitary, high-stakes, and requires a thick skin—traits that, let’s be honest, align pretty well with Wintour’s own career trajectory.
What Happened at the 2025 Tournament?
The 2025 US Open felt like a bit of a victory lap. With rumors constantly swirling about her future at Vogue, her presence at the tournament remained the one constant.
She was there for the mixed doubles final, sitting with Lin-Manuel Miranda. She was there for the Men's Final between Jannik Sinner and Taylor Fritz. She even braved the "Blue Carpet" events, which is unusual for someone who usually prefers to slip in through a side entrance.
One of the more surprising moments of the 2025 circuit was seeing her interact with the younger generation of players. She’s been a vocal supporter of the new guard, realizing that fashion needs tennis just as much as tennis likes the prestige of fashion.
Actionable Insights: The Wintour Guide to the US Open
If you're planning to attend the tournament and want to channel a bit of that Wintour energy—or just survive the day without melting—here is what the pros do.
Forget the Trends, Find a Uniform
Don't try to be "sporty" if you aren't. Anna proves that staying true to your personal style is more comfortable than trying to fit a theme. If you like dresses, wear a dress. Just make sure the fabric breathes. Linen and high-quality cotton are your best friends in the New York humidity.
The Power of the Shield
Invest in a serious pair of sunglasses. Not just for the "look," but for the eye strain. Arthur Ashe Stadium is massive, and the glare off the court is no joke.
Hydration vs. The Honey Deuce
The US Open is famous for the Honey Deuce (that vodka lemonade with the melon balls). They're great. Have one. But if you want to stay sharp for a night match like Anna, you need to match every cocktail with a liter of water. The heat in the stands can be brutal.
Arrive Early for the Outer Courts
The best tennis often happens away from the main stadium. Follow the Wintour method: check the schedule for the smaller courts. You get to be inches away from world-class athletes, and the atmosphere is way more electric than the upper tiers of the nosebleeds.
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Respect the Silence
Nothing marks you as a "newbie" faster than talking during a point. Wait for the changeover. It’s the one place where being "aloof" is actually the polite thing to do.
The Anna Wintour US Open presence is a reminder that the tournament is the ultimate intersection of grit and glamour. It’s where the toughest athletes in the world meet the most demanding editor in fashion, and somehow, in the middle of a Queens summer, it all makes perfect sense.