It's one of the biggest events in the British sporting calendar, sure, but it also brings out (every time, without fail) the very best of celebrity style. Of course, we're talking about Wimbledon, where every celeb takes to center court in the very best of their smart dress. And there's no accessory that rounds off a smart look quite like a watch.
From your typical, classic Rolex picks to newer (and even some unreleased) pieces, read on to see our roundup of the very best watches sported by the most stylish men at Wimbledon 2026.
The football legend is an ambassador for Tudor, so it isn't that surprising to see him sport one of its watches. What is exciting, however, is seeing the brand-new Tudor Black Bay 58 out and about in the wild. Especially considering that we named it one of the best new watches of 2026 so far.
Longtime Rolex ambassador, 20-time Grand Slam champion, and icon of men's tennis style. Roger Federer knows his fashion, and he certainly knows his watches. At Wimbledon this year, he brought back the iconic Rolex Datejust II that he sported during his 2009 Wimbledon victory, which won him his 15th Grand Slam title.
New watches? Sure, impressive. Unreleased watches? Now, that's how you cause a conversation. Over the weekend, Andrew Garfield sported an IWC Ingenieur Automatic model with a blue dial that watch spotters noticed was one that's supposedly set to be announced this week. Garfield is a man of mystery, and this proves it.
Football legends often know their watches, and Gareth Bale is no exception. His Rolex GMT-Master II watch, with a colorway that has been affectionately titled the 'Batman' watch due to its blue-black split. It's also a favorite among modern watch collectors, and for good reason.
We love the bigger, bulkier watches, but sometimes something smaller can look even more dressy. Ncuti Gatwa's tiny TAG Heuer Aquaracer Professional Solargraph 100 may be big in its name, but in a 28mm case, it's perfect proof that a watch doesn't need to be imposingly large to make a statement.
He's appeared twice at Wimbledon this year: once with a beautiful Patek Philippe Nautilus, and another time in one of his other go-to luxury timepieces. The second time around, Romeo Beckham sported his turquoise-dial Rolex Daytona – a grail watch for anyone obsessed with the brand.
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