Jannik Sinner Gucci
Clive Brunskill

UNLESS Carlos Alcaraz has hatched a plot to smuggle in a monogrammed LV duffle fresh from the Paris atelier, then the most notable Style Moment of the Wimbledon fortnight will have likely occurred on the tournament’s opening Monday, when Jannik Sinner, the men’s world number eight; a brilliant red-headed Italian 21-year-old with a monster forehand, the angular cheekbones of a model, and the cooly-focused gaze of an apex predator, strolled onto Centre Court with a custom Gucci kitbag slung over his shoulder.

Known for its stringent and polarising dress code (no ecru, cream or, lord forbid, a trim of colour larger than 10mm on any garments), it turns out that Gucci and Sinner’s team had met with the International Tennis Federation, Association of Tennis Professionals and Wimbledon to ensure that the bag met a certain set of mystery criteria (oh to be a fly on that war room wall).

Speaking to the New York Times on his headline-grabbing role in bringing a bit of Florentine high luxury into tennis’s grand cathedral, Sinner said, “I wanted the bag to be comfortable to carry and have enough to keep all my stuff inside.”

Thank you, Jannik.

Despite, or maybe because of its love of a rule, Wimbledon is still the most stylish grand slam. Gucci, Casablanca, Ralph, Armani, Celine, Lacoste… whichever brand references tennis in its designs will invariably lean on, refract, or subvert an element of ‘classic’ SW19 in its output. There’s a reason that, in 2018, Palace chose Wimbledon as the stage for its first foray into tennis clothing, collaborating with Adidas on a series of match kits, tennis balls and a quite nice towelling bucket hat.

Wimbledon Style
Palace x Adidas collection (2018) Simon M Bruty

A bit of red and white trim around the neckline and its name on the chest, it wasn’t exactly Stefan Edberg-level late eighties Adidas gear, but it was a statement, one that also birthed some typically great and glib product descriptions.




Players have learned to adapt, or flaunt, the rules. Last year, the combustible Nick Kyrigios felt that a fresh pair of Jordan 1s and a red cap were, in the interest of self-expression, worth being fined about the equivalent of a secondhand Corsa. “I do what I want,” he said when pressed on the issue by reporters. The great American, Andre Agassi, famously skipped the tournament for three years, writing in his autobiography, Open, that, “I resent rules, but especially arbitrary rules. Why must I wear white? I don’t want to wear white. Why should it matter to these people what I wear?

Agassi eventually relented, and won the whole thing in 1992. A son of Vegas, he learned that the house always wins. He also wore some great, slouchy Nike kit during his visits to London, and even a full over-the-head bandana with a goatee at one point, which was cool.

“Above all, I took offence at being barred and blocked and made to feel unwanted.”

Wimbledon Style
Andre Agassi (1995) Clive Brunskill

Sadly, the tournament seems to have only grown more dogmatic with its approach to all white. Leading up to the 2000s, there were some truly great, and often wild, outfits on regular display. Borg’s iconic pinstripe Fila polo and red track jacket, Pat Cash in a black and white headband, Ivan Lendl in Mizuno, an eagle emblazoned across his chest; the aforementioned Edberg in colour burst Adidas, and Boris Becker playing a whole Wimbledon final in a sweater vest. Arthur Ashe, the original king of tennis cool, did it first, with a giant-collared seventies polo shirt to match.

When Roger Federer was at his most imperious, he took to wearing monogrammed cardigans, white trousers and belted shorts on court— a look that would have been seen as totally ridiculous (still was a bit) if it wasn’t for the fact that he was putting his opponents through a blender in each round.

Wimbledon Style
Roger Federer (2008) Ryan Pierse

Even Federer, a diplomatic Swiss statesman to the very end, lashed out at the enforcement of all white when, back in 2015, he was punished for the terrible crime of wearing tennis shoes with orange soles.

I’m not going to mention the Nadal pirate look… but it was something. 

“I love Wimbledon,” he said, “but they’ve gone too far now. The rules have become ridiculously strict. I would be in favour of loosening it up a little bit. But it is what it is.”

Wimbledon Style
J.J. Wolf (2023) Clive Brunskill

It is what it is. Wimbledon will never budge, and players will continue to find ways of sprinkling in their own personal style amongst the clean classicism of the tournament… or at least work out how to bring a really nice kit bag on court with the help of the ITF, the ATP, and the power of Gucci.

That tension, the old, the new, and the intractable, is what makes Wimbledon the best, and best-dressed, tournament in tennis.

This article originally appeared on Esquire US.

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