The Best-Dressed Tennis Players of All-Time – Esquire
From fashion week catwalks to SW9 wardrobes, the appeal of tennis fashion endures. There’s just a gracefulness to it, the kind of easy elegance that can offset the sad fact that you’ve whacked yet another ball into a nearby cemetery. What says ‘I’m on top of my laundry and have time for extra-curricular sports’ better than a fresh set of creaseless, spotless tennis whites? And even if you’re not dressing for Wimbledon, a Palmes polo shirt and Casablanca shorts combo reads off-duty athlete while still being acceptable attire for a pub pitstop. All in all, there’s a genteel, preppy attitude that underlines tennis and its uniform – which is a lot more approachable than football’s brash approach and rugby’s irritating rah-ness.
But it’s the sport’s prim and proper outlook that tennis newcomers have come to question, as highlighted in new Netflix’s Break Point. The docu-series follows some of the new racket-wielding stars as they endeavour to become household names like the legends of yesteryear. The behind-the-scenes viewpoint highlights players’ mental health struggles and the sport’s impact on their personal relationships – making it an easy entryway for those who think of Stan Smith as a mysterious face on a sneaker tongue.
To celebrate the show that gives the fashion-conscious some contextual knowledge to whip out for any Grand Slam-centred discussion, we’ve highlighted some of the best-dressed players in the sport’s history.
In the ‘70s, Borg was the first man to pick apart the traditional dress code of tennis. With long blonde locks, a striped sweatband and a constant rotation of disco-inspired ‘fits, the Scandinavian was a hit on and off the courts, and decades later he was the inspiration behind Richie Tenenbaum in Wes Anderson’s cult classic, The Royal Tenenbaums. He was most recognisable for his Fila endorsement, that saw him wear track tops initialled ‘BJ’ and his famous Fila Settanta Mk1 polo shirt. But his fashion-forward status was cemented when he started his own line in 1984.
You don’t often see social activism and sport overlap, but that was the case for Arthur Ashe. Not only was he the first and only Black man to win Wimbledon in 1975, but the tennis player also dedicated his life post-retirement to civil and human rights, using his platform to help fight apartheid in South Africa and create inner-city tennis and employment programmes for the younger generation. To boot, he also had immaculate style. Ashe proved why a traditional tennis look was and will always be cool, keeping to a uniform of neutral polo shirts and shorts that were accessorised by square-frame glasses and a simple gold chain. Emulating his look couldn’t be easier; the creative minds behind Rowing Blazer’s launched a brand in his honour last summer.
As renowned for his temper (move over Kyrgios) as his supreme volleying on the courts, McEnroe is a memorable character with a catchphrase – many remember him shouting “You cannot be serious?!” to a Wimbledon empire in 1981. As a regular rival to Borg, his look too was in the same class: a red sweatband would often cover his curly barnet, completing a track top and short shorts combo. The clear sartorial difference between the two players? McEnroe would be spotted with a pair of sports socks pulled high.
It’s unusual to hear of a sportsman who wholeheartedly hates the sport they play, but Andre Agassi was one of them. Pushed onto the court by an overbearing father, the player – who proved that you don’t have to love something to be good at it – rebelled through his outfit choices in the Eighties and Nineties, even refusing to play at Wimbledon for a few years due to its traditional all-white dress code. This resulted in looks built around acid-wash shorts, a memorable mullet, block-print polo shirts and colourful sunglasses that brought an anti-establishment air to the tennis scene. It was so striking that Nike brought back the designs in 2020, working with Agassi to create a 21st century version of his renowned Challenge Court collection.
As well as tremendous style kudos, Eighties tennis star Yannick Noah – nicknamed Tennis Rastelli – is equally as well-loved his is hair evolution, which went from a short Afro to dreads that bobbed to and fro while he played. As still the only French player to have won the French Open, Noah is of national hero status – even more so when he wore a David Bowie tee during his practice rounds at Wimbolden, rebelling in true French fashion against the championship’s traditional attire. Le Coq Sportif also has him to thank for bringing the brand into the mainstream, later renaming his Crescendo wooden racket to the Noah Pro in his honour. And to top off his cool credentials, Noah moved onto music after retiring from tennis.
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