These are the most stylish tennis players in history

From Bjorn Borg and his open collars to Roger Federer’s knitwear collection, we take a swing at rounding up the sport’s six most stylish players…

For decades, tennis has been a painfully stylish sport. Since racquets first swung on the world stage, athletes have been serving up looks that push their athletic attire to its limits. Think Ilie Natase’s chic association with Adidas. Or Yannick Noah’s smashing stripy tops. And the hair! From McEnroe’s perm to Gustavo Kuerten’s curtains, there have been more shaggy styles on the court than we — or even the most diligent Chair Umpire — could ever keep count of. 

But it’s off-court fashion that we’re really interested in. Anyone can work wonders in white at Wimbledon — but it takes a true maverick of the sport to make an impression when the sweatbands are off. Below, we’ve rounded up six professional players whose signature styles managed to evolve beyond the baseline…

Bjorn Borg’s chains demanded open collars

The first male player to win five Wimbledon titles during the Open Era, Bjorn Borg’s success rate is the stuff of modern tennis legend (second only, perhaps, to his luxuriant locks). The Swedish former world No. 1, Borg had a style that was less Scandinavian, and more ‘south of France’. With a collection of fine chains, he only ever used around half the buttons on his shirts; showcasing his jewellery and chest in equal record-setting measure.

It’s a style you should look to replicate this summer. The first step, of course, is to find a chain that sits nonchalantly around your neck — nothing too glitzy or ostentatious, but rather subtle, such as Bottega Veneta’s gold-plated option. Then throw on a quietly-patterned or block colour shirt (you’ll never go wrong with either Turnbull & Asser or New & Lingwood for this), and do up three or four buttons. Sorted. 

These are the most stylish tennis players in history

New & Lingwood Striped Tailored Shirt

£125

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These are the most stylish tennis players in history

Bottega Veneta Gold-Plated Necklace

£430

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These are the most stylish tennis players in history

Turnbull & Asser ‘Dr. No’ Shirt

£250

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Arthur Ashe was made to wear shades

Tennis icon Arthur Ashe was not only the first black player in history selected to the United States Davis Cup team — he also remains the only black player to ever win the singles titles at Wimbledon, the US Open and the Australian Open. It’s an important, enduring legacy — and a stamp on the sport that’s nicely framed by his own extraordinary collection of frames. Because Ashe was an accessories man; and he loved a pair of sunglasses.

In every image you see of the Virginia-born tennis pro, he seems to be wearing a different pair. But, whether these are square in shape and mottled in tortoiseshell, or wire-rimmed, green-tinted aviator sunglasses, Ashe was a man who deployed each statement pair at the perfect, most measured moment. The lesson here? Invest in the best, from brands including Oscar Deen, Monc and TBD Eyewear — and match your specs to your daily style. 

These are the most stylish tennis players in history

Oscar Deen ‘Fraser’ Sunglasses

£135

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These are the most stylish tennis players in history

TBD Eyewear ‘Denim’ Glasses

£135

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These are the most stylish tennis players in history

Monc ‘Príncipe’ Sunglasses

£230

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Fred Perry had the nattiest knitwear on the court

In 1984, a statue of Perry was unveiled outside Wimbledon — but we’re surprised it took so long. The Stockport-born sportsman was a titan of tennis, becoming the first player to achieve a ‘Career Grand Slam’ (at the age of just 26 in 1935), winning 10 Majors and even becoming World Table Tennis Champion early on in his career. He’s also the only athlete on this list to lend both his name and expertise to an actual fashion brand. 

So what can we learn from the grandfather of British tennis? Like many men of the era, Perry had a penchant for fine knitwear — both on and off the court. Similar to cricket sweaters (such as the below by N. E. Blake & Co.) Perry would wear tennis sweaters; off-white, cable-knitted pullovers with deep contrast v-necks. We’d keep the cream colour, but recommend experimenting with designs, such as something plain from New & Lingwood — or this statement ‘Skipper’ jumper from Hemingsworth. 

These are the most stylish tennis players in history

N. E. Blake & Co. "Brian Close" Cricket Jumper

£139

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These are the most stylish tennis players in history

Hemingsworth ‘Skipper’ Varsity Jumper

£365

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These are the most stylish tennis players in history

New & Lingwood Silk Jumper

£295

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Andre Agassi capped his career with some serious headgear

During Agassi’s time at the top, the American athlete was known as ‘The Punisher’. Following Fred Perry and three others, he became the fifth tennis player in history to achieve a ‘Career Grand Slam’ — and remains the only man in history to secure the coveted ‘Super Slam’ (which also includes a win at the year-end championships and an Olympic Gold). And he did all of that whilst serving some of the best on-court looks in history.

There were bold, block coloured shell-suits and tight, bright neon undershorts. There were short shorts and even shorter shorts, lion-mane mullets and thick patterned sweatbands. But his most trusty accessory was the humble baseball cap — admittedly adopted from another sport, but worn both on and off the court. To ape Agassi, stick with subdued colours, like the navy of David Gandy Wellwear or beige of Ralph Lauren, and small, subtle logos — like this ‘D’ cap from Drake’s. 

These are the most stylish tennis players in history

David Gandy Wellwear Heritage Cap

£35

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These are the most stylish tennis players in history

Ralph Lauren Cotton Chino Ball Cap

£45

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These are the most stylish tennis players in history

Drake’s Navy ‘D’ Flag Cap

£55

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Trim tailoring was John Newcombe’s strong suit

If you’ve never heard of John Newcombe, then shame on you. Because not only did the man have a moustache you simply couldn’t miss, he was also one of the finest Australian athletes in the world during his horseshoe-combing heyday. One of the few players in history to achieve a world No. 1 ranking in both singles and doubles, he won 26 major titles across the disciplines during his career. But we’re most impressed with his work off the court.

Because, whilst many players spend their off-duty days in sweats, Newcombe knew his way around a finely crafted suit. Whether he was donning velvet-trimmed black tie or slipping into a slightly-flared, height-of-fashion pinstripe number, the man had his tailoring down to a tee. His secret? Keep things simple. Follow suit, quite literally, with a pared-back Ermenegildo Zegna two-piece, over an Emma Willis and Drake’s shirt-and-tie combo. 

These are the most stylish tennis players in history

Ermenegildo Zegna Midnight-Blue Suit

£1720

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These are the most stylish tennis players in history

Emma Willis Superior Cotton Shirt

£200

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These are the most stylish tennis players in history

Drake’s Green Tile Print Tie

£145

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Roger Federer’s sweater collection is a grand slam

And, finally, Federer. ‘The Swiss Maestro’ really needs no introduction — considered by many to be among the greatest tennis players of all time. But some brief stats anyway: he’s been ranked world No. 1 for 310 weeks (237 of them consecutively); he won his first major singles title, at Wimbledon, at the age of just 21; he completed his ‘Career Grand Slam’ in 2009. And he really, really knows how to wear a turtleneck.

As the most modern player on this list, Federer’s career has been the most scrutinised off-court and on social media. In this new age of ‘celebrity sportsmen’, invitations to galas and red carpet events began to roll in — and so Federer had to look the part. Thankfully, his formalwear has always stuck to a formula; pick a good turtleneck jumper (we’d look to Shackleton, Luca Faloni or Sunspel for this), pair with a suit, and repeat. 

These are the most stylish tennis players in history

Shackleton Centenary ‘Hero’ Sweater

£225

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These are the most stylish tennis players in history

Luca Faloni Rollneck Jumper

£275

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These are the most stylish tennis players in history

Sunspel Fine Merino Roll Neck

£175

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Looking for more style tips? We asked 10 Italian style influencers to define the term ‘sprezzatura’…

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