The most stylish tennis players of all time
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Tennis style icons

The most stylish tennis players of all time

Words— Marc Richardson

The U.S. Open is upon us. While Wimbledon’s grounds may be the most hallowed in the sport of tennis, there is something magical about the U.S. Open that no other tennis tournament can match. Maybe it’s the night matches that go late into the night — we’re talking until 2 A.M. — and make for riveting primetime and late night television. Perhaps it’s the fact that there is always someone who goes on a magical run at Flushing Meadows — Juan Martin Del Potro snapped the Big Four’s dominance a the U.S. Open and Kei Nishikori and Marin Cilic locked horns on Arthur Ashe Court in the first Grand Slam final in ages that didn’t feature one of the Big Four.


That’s all fine and dandy, but, let’s be honest, most people would rather see Federer vs. Nadal than Nishikori vs. Cilic, so the magic can’t be attributed to deep runs by virtually unknowns. No, instead, what makes the U.S. Open great is that it encourages players to be themselves and to be as loud and boisterous as possible. It’s where the outfits are the most daring — compared to the stuffy all-whites of Wimbledon and the catsuit-deprived French Open, that might not be saying much, though. It’s where individuality shines and where players ruffle the feathers of the tennis establishment.


So, with that in mind, we felt that this was as good a time as any to pay homage to the style pioneers of the game. Those who dared to challenge the status quo, or who managed to put their own spin — within the rules — on traditional club-appropriate attire.

Björn Borg




Björn Borg was tennis’ first true star. Sure there were great players before him, and well-dressed ones, too — René Lacoste and Fred Perry even went on to launch stylish clothing brands themselves —, but Borg was different. In many respects, he was the antithesis to his contemporary, John McEnroe. Everything about Borg oozed effortless cool, including his wardrobe.


The stylish Swede dabbled with Slazenger, adidas, and Fred Perry before becoming the face of FILA’s tennis endeavours in the late ‘70s. He became a champion of both the game, but also of a brash preppy style that infused just enough personality into time-honoured classics. He’d wear white polos — but they’d be accented with colourful colours and pinstripes, with colour-coordinated headbands and short shorts rounding out the look.


His personal style became the inspiration for Wes Anderson’s Richie Tenenbaum. The guy’s style is iconic and inspiring, even if you don’t immediately recognize it. More importantly, though, he helped normalize the fact that tennis players could express themselves through their on-court threads.



The Sisters Williams




Venus is definitely the more stylish of the two Williams sisters, but Serena deserves an honourable mention based solely on her proclivity for catsuits and the fact that she played in a blazer at Wimbledon. Of course, the fact that she now rocks Nike x Off-White on court and graces the back cover of Vogue’s September issue shouldn’t be overlooked, either.



But, that being said, style is the one area where Venus reigns supreme over her sister — Serena is, arguably, the most dominant athlete of all time, regardless of sport or gender. Venus harbours ambitions of becoming a fashion designer and she already has a signature line of on-court garments that have been hard to not ignore over the last few years. Her own outfits are daring and deserve attention, but some of the greatest looks came when she was sponsored by Reebok — possibly off the strength of the sneakers alone.

Above all else, though, Venus’ signature style moment may have come early in her career, when she wore multi-coloured beaded braids and even coordinated them based on the tournament.



André Agassi




If Borg was tennis’ first true star, then Agassi was the sport’s first anti-hero. He was a rebel, challenging the steeped-in-tradition tennis establishment.


Agassi had flair, that much was undeniable. The man was impossible to miss and infused the game of tennis with neon colours beyond just the balls used to play the game. Seriously, his sartorial achievements are so many that it’s hard to do more than just list them all.


He wore denim shorts on court. He wore biking shorts under his tennis shorts, single-handedly making them cool before Kanye West and Kim Kardashian turned biking shorts into a fashion item. He rocked razorblade sunglasses better than anybody. And his signature Air Tech Challenge sneaker is arguably the most iconic sneaker to come from the tennis court aside from the Stan Smith — the air unit is the same used on Nike’s Air Yeezy 2.



It’s hard to look at it as accidental style, though. Agassi’s flowing mane was as much a staple of his persona as his style was, but he later revealed that it was a wig. It was all part of an intentional masterplan to brand himself as tennis’ aesthetic bad boy.


Even in his later years, when he had less hair and a more subdued sartorial inclination, Agassi found a way to express himself and stand out from the rest of the field, sporting all-over print shorts, baggy polos and paisley bandanas that was equal parts pirate and municipal tennis rat.



Roger Federer




Roger Federer’s style is not as flashy as Agassi’s, or even Borg’s. But what Federer lacks in pizzaz, he makes for in class. In that respect, Federer represents the epitome of traditional tennis style.


The Swiss maestro looks at ease in his crisp all-whites on the grass courts of Wimbledon, but he’s also willing to try some more daring outfits. He famously opted for a military-inspired three-piece suit combination at the All-England Club, which, while curious, was definitely adventurous. He’s also tested the rules, with neon-inflected sneakers ruffling a few too many feathers at Wimbledon and leading the tournament to ban them.



Many of his greatest style moments have come in New York, where he has rocked all-black Nike outfits and debuted limited edition takes on his signature on-court sneaker inspired by cultural sneaker heavyweights like the Air Jordan 3 Black Cement. Plus, the bandana-headband hybrid’s popularity owes a great deal to the greatest man to ever play the game — yes, we went there.


Perhaps nowhere are Federer’s style credentials more obvious than when he’s off-court, something which helps set him apart from his contemporaries. At galas and events, Federer has dazzled in tuxedoes and turtlenecks, as well as more casual outfits. Yes, the man probably has the benefit of a personal shopper, but whoever is responsible for branding his wardrobe deserves praise. Wait, Anna Wintour is his style mentor? Yeah, never mind the praise, she’s gotten enough.


But, Federer is not above reproach. Even the most perfect among us are still imperfect.



Dishonourable mention: Rafael Nadal




For the life of me, I can’t comprehend why Rafael Nadal features on some of the “best-dressed tennis players of all time” lists. Is he the most improved dresser in the sport’s history? Absolutely.


But even now, he isn’t among the great sartorial icons of the game. He doesn’t look comfortable — which is something that is a must to be a style icon — and he hasn’t really done anything drastically different or noticeable. Nike outfits him with some interesting colour combinations, but the man has perfect skin, so obviously it’s going to look good on him.


Really, we’ll always remember Rafa for his capris and sleeveless tops.