The problem with tennis, if it has one, is that its image has just been too good. Its elegance, epitomised by those traditional tennis whites, has often been perceived as a certain staidness. And yet there is a brutality to tennis, which no number of friendly handshakes at the net erases. It’s this mix of niceties and cruelties that makes it great. Or, as Ms Billie Jean King once put it, it’s “a perfect combination of violent action taking place in an atmosphere of total tranquillity”.

A similar dichotomy exists among the game’s most stylish players. There is, of course, a classic look, which traces its origins to the legendary Mr Fred Perry and lives on today in the persona of Mr Roger Federer, whose well-nurtured classical wardrobe neatly reflects his style of play. Elsewhere, players such as Mr Rafael Nadal boldly play with colours and sleeves and short lengths, with varying levels of success. Inevitably, the greatest style icons of the sport lie somewhere in between. They’ve often been rebels, but not always in the showiest way. Tennis doesn’t necessarily reward the one who hits hardest, more the one who hits between the lines.

It’s hard to overestimate the impact Mr Andre Agassi had on the sport. A teen prodigy from Las Vegas, Mr Agassi had sponsorship deals long before he ever won a Grand Slam. In fact, the tagline of one of his adverts, “Image is everything”, seemed like a premonition. He eventually put that right, winning Wimbledon in 1992 and then going on to win seven other titles, conquering the championships on every surface.

Fashion-wise, he was just as versatile. The early Mr Agassi look was a thorough flouting of the conventions of tennis. He avoided Wimbledon for a long time, not just because of its tricky grass courts, but also for its dull all-white decree. To wit, Nike’s designs for Mr Agassi were described thusly: “A series of acid-wash denim shorts with neon yellow, pink and purple Lycra tights underneath extending mid-thigh. The accompanying top was loosely fitted with a pull zipper instead of the traditional three-button polo, and featured colourful geometric shapes.” There are traditionalists for whom this is beyond the pale, but one can’t deny it showed panache. Or the influence on a whole generation of modern clubbers and festival-goers, for that matter. Mr Agassi eventually won his greatest trophies when he got smarter and more serious, but there’s no doubt that the prevailing image of this icon dates from much earlier, back when he was busy snubbing the relentless good taste of tennis and instead embracing the bright colours and bold looks of 1990s fashion.

Exuberance is great, but there’s also a lot to be said for sheer class. Mr Arthur Ashe was the ideal ambassador of this – and still is, more than 25 years after his death. Born in 1943 in racially segregated Richmond, Virginia, the future triple Grand Slam winner had to overcome innumerable obstacles to succeed. He was even taught to play any ball that bounced two inches from the lines, in or out, on the assumption that he wouldn’t necessarily get the right call.

Mr Ashe became a spokesman and a pioneer of civil rights and racial equality. Later on, when he contracted HIV from a blood transfusion (he died of Aids-related pneumonia in 1993), he became an advocate for HIV awareness, too. His clothing – classic, elegant, restrained – went hand in hand with his persona, but it would be wrong to think of Mr Ashe as a bland saint. He knew the power of the right accessory, principally his signature glasses, either thick-rimmed square specs or aviators. He loved a gold watch and zip-up jackets in all colours. Basically, he knew how to express himself and have fun with his clothes. And in 2019, he’s still ahead of the curve, remaining the only black man to have won the singles at the Australian Open, the US Open and Wimbledon.

Mr René Lacoste was one of the Four Musketeers, a group of French players who dominated the sport throughout the 1920s and 1930s. Each had a certain flair, not least Mr Henri Cochet. But Mr Lacoste has retained an edge, thanks to a certain crocodile he once had sewn onto his shirts. Its origins lie in a bet. Mr Lacoste’s captain wagered that if he won his upcoming match, he’d buy him a beautiful crocodile-skin suitcase. Mr Lacoste lost the match, but gained a brand from it. A journalist reporting on the story handed it to him on a plate. “The young Lacoste has not won his crocodile-skin suitcase, but he fought like a true crocodile.” He took the name, and image, and ran with it.

Mr Lacoste managed many inventions in his lifetime (he helped to patent one of the first steel-frame rackets, sending wooden versions on their way). His first innovation, though, had been to wear short-sleeved, three-button shirts to play tennis, which were much more freeing and breathable than the traditional, long-sleeved button-down shirts his peers wore. His second was to emblazon the crocodile motif on said shirts. And his third was to launch his own range in 1933, the advert proclaiming that they were “for tennis, golf, the beach”. Today, more than 80 years on, this is still true.

The chief virtue of Mr Björn Borg as a player was to be almost machine-like, each shot coming back the same way. For his peers brought up on a classic diet of drop shots, dinks and slices, it was a shock – a big enough shock to bag him 11 Grand Slam titles, including five consecutive Wimbledon wins.

Mr Borg dressed like he played, consistently and successfully, but with a surprising edge. The formula was simple: long blond hair, striped headband, a physique that was mostly Scandi health freak with a touch of Greek god, a neat polo shirt and some truly short shorts. The look persisted long after Mr Borg retired, from Mr Luke Wilson’s get-up in The Royal Tenenbaums all the way down to the eveningwear choices of the lads on Love Island.

Style isn’t always flamboyance and flamboyance isn’t always style, but in Mr Boris Becker’s case, the two are very much the same thing. The German star has always had an outsized quality to him, on court and off. The same energy that helped him secure his first win at Wimbledon as a 17-year-old has helped him try various other careers, face the odd bankruptcy and enjoy tabloid infamy.

Mr Becker has never quite been your archetypal German, and the same goes for his clothes. Sometimes they were tight, the shorts especially. Later, they got loose. Proportion was never his thing, but he could wear anything, safe in the confidence that muscular thighs, full lips and a permanent twinkle in his ice-blue eyes would help him carry off most things. Perhaps his greatest achievement is his strawberry-blond hair, which has gone from a youthful bob to a well-carried mullet to a rigorous Teutonic buzzcut. Mr Becker has always had a certain charisma, which has carried him through, beyond the court.

The people featured in this story are not associated with and do not endorse MR PORTER or the products shown