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Best-Dressed Woman at Wimbledon 2025 – Little Yellow Ball

Best-Dressed Woman at Wimbledon 2025 – Little Yellow Ball


Have I resolved the technical issues that plagued last week’s face-off? I hope so. My apologies for the less-than-seamless reading experience — and thank you to those who valiantly forged ahead anyway. Give a shout if there continue to be problems.

Now on to the women of Wimbledon…

Did you happen to catch commentator Pam Shriver speculating that Jessica Pegula was on the rag during her surprise first-round loss?

If I can come up with a theory here. A few years ago, the club allowed the women players to wear colored tennis pants if they choose to — and Jessie is today. We all have to realize that cycles are a part of what we have to deal with… She looks like a different player from the final two days ago.

–Pam Shriver

I have to say, I’m a little embarrassed. All this time I’ve been prattling on about fashion on the basis of mere aesthetics, completely oblivious to the hidden meaning in details like colored shorts. I mean, I was a grad student in English, for crying out loud! Ferreting out symbolism and concocting theories based on the flimsiest of evidence was basically my entire life for years. How could I have overlooked the rich interpretive opportunities tennis fashion affords?

I’m going to try to do better this time around, but I’ll admit upfront: Pam Shriver’s commentary is going to be tough to beat.

Nominee #1: Naomi Osaka

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No doubt the old me would blather on about the beautiful weaving on the bodice and the lovely drape of the skirt. Old me would probably go off on some tangent about pleats, how they can look stiff and add bulk when they’re done poorly and how exquisite they can be when done well. I’d then wrap it all up with some pithy banality like “Elegance in motion” or “A triumph of texture over color.” So shallow. So cringeworthy.

But as Shriver has so memorably shown, we can look beyond the surface and read this dress as text. What is it saying about Osaka? What might it indicate of her inner turmoil? I’d argue the tight interweaving of fabric over her abdomen suggests a sense of vulnerability and a desire to protect this most sensitive region with a kind of armor. This may point to a psychological vulnerability, something Osaka has openly addressed in the past. On the other hand, the bodice structure could represent a cradling of a physical ailment. Maybe she has some sort of digestive disorder, like irritable bowel syndrome, which could explain her third-round upset.

She does look a little irritable, come to think of it.

Nominee #2: Emma Navarro

Embed from Getty Images

Embed from Getty Images

In a sea of bland Nikes, the young American star is a standout in this fresh Fila ensemble. Beautifully cut and fitting to a T, it all but screams country club living. Somewhere on the veranda, gin and tonics are being served.

Still, my eye can’t help but be drawn to the pleats inset on only one side of the skirt. Lovely, yes, but why the imbalance? Why not pleats for both sides — or even all sides? Could it be the billionaire’s daughter is making a subconscious statement about our country’s wealth inequality? Much as she claims she wasn’t raised spoiled, her clothes speak to a deep-seated ambivalence about her privilege. Look at the second photo — she’s literally hiding her face in shame.

(Let the record show that LYB is wealth-neutral, if not downright pro-billionaire, so please don’t unsubscribe if you happen to fall in this lucky bracket.) (Also, contact me for sponsorship opportunities.)

Nominee #3: Marta Kostyuk

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The 18th seed from Ukraine looks perfectly proper and unremarkable here, doesn’t she? Nothing to see here, don’t mind me.

But then she turns around…

Embed from Getty Images

Whoa. That’s a lot of skin for Wimbledon.

I was on the fence about this two-faced dress initially. Maybe I needed more time for it to grow on me, but Kostyuk crashed out too quickly for that.

But our keen Shriver-esque critical powers help us see this Wilson dress in a new light. Far from uneven and inconsistent, the dress can only be seen as an eloquent tribute to Kostyuk’s war-ravaged country: mild-mannered, unobtrusive, and — just when you least expect it — capable of drone-bombing the crap out of your warplanes. Underestimate Ukrainians at your peril.

Well, that was fun! Join us next week for a statistical analysis of the proportion of women wearing colored shorts and the extent to which the ladies on tour have synced up their cycles!

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