The Carolyn Bessette, Gabrielle Chanel Effect

What I've learned about dressing for tennis tournaments so far…

Each time I attempt to plan my outfits for tournaments I've never been to, nine times out of ten it's a total miss. I end up packing one thing, then buying something when I arrive because I realize I've packed completely the wrong thing — or suddenly we're halfway through the day and I'm begging Charlie to buy me a workout set from the gift shop because I've sweat through my entire outfit. When I break it down, there are several factors at play: I'm doing too much, I don't know what to expect, I don't know the "vibe" of the tournament, and I'm totally guessing on weather. But the number one thing I always get wrong? I trust the internet — more specifically, I trust influencers.

I talk about this in my first blog, "The Reality of Tennis Fashion" — the difference between us regular girls attending the US Open versus the influencers, the girlfriends, or the "somehow got invited to a suite important people." The question is always: where do I fit into all of this, when what I see online is just not what I get in practice? For example, they might be going for one match, staying on a single court, with nice enough seats to be in the shade all day — or if they're in a suite, the food is provided. The luxury of watching tennis from their point of view is just different. So ever since 2024, I've been trying to crack the code on dressing for tennis tournaments, and here's what's on my mind.

There's been a lot of controversy, love, and inspiration circling recently around Carolyn Bessette-Kennedy following the new Hulu show Love Story. Suddenly the girls online want to dress like her and are finding ways to replicate her '90s minimalistic style. During this frenzy, it made me wonder how a "movement" like this could relate to or inspire dressing for tournaments — because the truth behind Carolyn's style has less to do with logos and flashy trends, and everything to do with reliability, wearable essentials, and above all, comfort. A designer and close friend to Carolyn, Narciso Rodriguez said, "Her style was never a production. It was just something innate" (ELLE Magazine, April 2025). Which is another way of saying: the way Carolyn dressed was something she felt she could always count on. Whether or not that was a conscious thought of Carolyn's, it's hard to talk about the freedom and comfort of dressing without bringing up its original trailblazer: Gabrielle "Coco" Chanel.

It might seem odd to pivot from dressing for tennis tournaments to one of the most influential couturiers of the 20th century. But outside the boutiques and behind the large price tags are accessible, democratic ways of thinking about fashion. Coco Chanel's rebellion was born from a desire to make clothes that gave women the freedom to move in their own bodies — liberating them from corsets to menswear-inspired tailoring, from dresses to pants. Something functional, yet still luxurious.

So how do the design philosophies of these two icons apply when thinking about how the average tennis spectator dresses for tournaments? When we still want to look as cute as the girls in the players' boxes, but two sections up, five hours, and 20,000+ steps later? I'm no expert, and I'm certainly not Coco Chanel, but here's what I'm observing.

Even Chanel Wore Pants

Just because you look online and see everyone in pretty dresses frolicking around the grounds doesn't mean you have to. Actually, I've tried it, and I'm here to tell you: it's a terrible experience. You're either so sweaty you're sliding off your chair, or you're sitting on metal bleachers and branding the backs of your thighs. Don't fear the look of a nice pair of slacks — or in Carolyn's case, the loyal Levi's 517s.

Sunglasses

I once tried to show my hairdresser a photo of Charlie and could barely find a single one without his sunglasses on. Then I realized how much time we spend at tournaments — in the sun, or in overcast light — needing our sunglasses just to watch the match. Carolyn had a beloved pair from Selima Optique that she wore with nearly every outfit, so much so that they later named them after her! At a tournament, sunglasses can be a real anchor for any look.

Statement Sneaker

Did you know the iconic Chanel slingback was designed with a black toe cap specifically to prevent scuffing? Another practical detail from a founding mother of fashion. Shoes are, unfortunately, make or break at a tournament. No matter how many times I tell myself "I'll be fine in these shoes," Charlie ends up rolling his eyes at me. Advice I've seen (and for some reason never taken) is to find an amazing statement sneaker and let it become the most understated yet versatile piece you have on.

The 2.55 Bag

In 1955, Chanel launched the "2.55 bag" as their luxury answer to a more accessible purse design. It came with a shoulder strap (earlier designs were clutches that could only be carried by hand) and an iconic outside flap pocket for your $$$. It was all around completely practical. Now, I'm not saying go buy a Chanel bag, but if you have the money, you go girl. What I am saying is that at tennis tournaments, you have the fun (?) task of getting creative — especially on the American swing — around bag policies. Unless you've got a 2.55-gallon clear bag, you have to follow very strict dimensions for your purse. So far, Indian Wells has the worst restrictions I've seen (more on that in our guide). But, just like Chanel, I know you'll all rise to the challenge and find a purse that matches your outfit impeccably, with at least enough room for your lipstick.

High-Low

Similar to Carolyn, I'm not a big jewelry person, and back in the '90s, neither was Chanel, kind of. In the world of Haute Couture, "costume jewelry" was considered cheap and tacky. To Chanel, this was just another opportunity to redefine a common practice she considered malpractice. She believed women should mix real jewelry with faux jewelry — "high with low" — and that the point shouldn't be to make a woman look rich, but to make her look adorned, which in her book were not the same thing. I bring this up not to talk about jewelry specifically, but to say: when it comes to dressing for tournaments, you don't have to go out and buy expensive clothes, bags, shoes, or anything at all. But if you'd like a more intentional approach to shopping — one that isn't just buying everything on the cheap — consider the high-low method: expensive sneakers with pants from Zara, nice sunglasses with a secondhand dress, or Charlie's personal favorite: a really nice purse with shoes from Target.