The Best-Dressed Male Tennis Players of All-Time

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.