"Tennis is now cool again," read a tweet in response to Palace and adidas' collaboration at last year's Wimbledon. The two brands coming together on tennis' most hallowed stage represented a watershed moment for streetwear and sport. A couple of months later at the 2018 US Open, the relationship tightened when Serena Williams stepped out wearing Nike apparel and sneakers designed by Virgil Abloh.

This year, it’s young Japanese superstar Naomi Osaka who has stolen the headlines, at least sartorially, after it was revealed she will be taking to the court in a sacai x Nike outfit designed by Chitose Abe.

While the commercial importance of these collaborations cannot be understated, the likes of Palace and Off-White™ aren't some sartorial white knights that have arrived to propel stuffy old tennis into the realm of cool. Sure, they add a street-smart edge, but tennis is a sport with a style heritage that stretches back to the 19th century. Tennis has always been cool, playing an influential role in shaping menswear as we know it today.

With the 2019 US Open well underway, we take a look back at some of men's tennis' most fashionable rivalries.

René Lacoste vs. Fred Perry

Getty Images / Topical Press Agency / Davis Getty Images / Topical Press Agency

We start with one of the most ferocious rivalries in all of tennis — one in which the two players never even played a professional match against each other.

The story begins in Victorian-era England, where white clothing, like the sport itself, was a status symbol of the rich. If you wore white, it meant you had money, making it easier for the upper classes to sort the merchants from the miners. In 1890, the All England Croquet and Lawn Tennis Club mandated that players at its tennis tournament in Wimbledon, London wear all-white on court — a tradition that still exists today.

As the 1920s roared, tennis started to loosen up, eschewing prim attire in favor of more adventurous, looser fits. As young men returned from World War I, out went three-piece suits and other restrictive clothing deemed out of step with the Jazz Age. Bill Tilden, the world's proto-prep and tennis' first real star, became an icon with his V-neck sweaters and flash bravado, while women swapped their long skirts for sporty dresses and headbands.

One of the sport's dominant forces at this point was René Lacoste, a Frenchman nicknamed "The Crocodile" (a mistranslation of the "Alligator" nickname given to him by an American journalist). Lacoste used his engineering background to invent the first steel racket and tennis ball machine. More importantly, Lacoste introduced players to lightweight collared cotton shirts (polo shirts to you and me) in 1933, which — as Sports Illustrated put it in 1965 — replaced "the starch, cuffs, and collars of an earlier day." Today, the brand emblazoned with the crocodile is still going strong, with incumbent Wimbledon champion Novak Djokovic its current frontman.

Getty Images / Topical Press Agency

As Lacoste entered retirement from playing after winning his third French Open in 1929, a future star by the name of Fred Perry was getting started on the other side of the English Channel. In terms of personality and background, the duo couldn't have been more different: Lacoste was a quiet-living introvert from a middle-class background; Perry was a working-class, four-times-married playboy whose fame led him to date the likes of Marlene Dietrich and Jean Harlow. What the pair did have in common, however, was a talent for innovation.

To combat perspiration flowing from arm to racket, Perry wrapped medical gauze around his wrist. Eventually, in the late 1940s, he befriended Austrian ex-footballer Tibby Wegner, who helped Perry transform his makeshift wrist towel into the world's first sweatband. By the time the ’50s rolled around, Perry and Wegner moved into clothing, producing polo shirts not entirely unlike Lacoste's.

Perry and Lacoste might have given tennis the polo shirt, but it was British subculture that adopted it. When Caribbean immigrants mingled with Cockney lads in London, they introduced them to ska and rude boy style: a preppy, anti-hippie look that mixed clean cuts with smart Levi's jeans and heavy Doc Martens boots. The look — usually topped off with a polo — was razor sharp but prided affordability, separating it from more well-to-do mod culture (they were initially known as "hard mods" before the term "skinhead" was introduced).

Later, as the ’70s and ’80s roiled the UK socially and economically, and the skinhead movement spread, the far right saw an opportunity to recruit groups of angry and disillusioned young men. The National Front, a rapidly growing white nationalist political party, would set up shop outside football stadiums and infiltrated the UK punk scene. The understanding of what a skinhead was changed dramatically. Elsewhere, hardcore football fan groups, known as casuals and defined by their uniform of branded clothing, were battling for superiority inside and outside stadiums every Saturday.

Getty Images / PYMCA / UIG / Getty Images

"You can trace tennis wear being re-appropriated by youth culture back to the Fred Perry polos worn by skinheads and football hooligans in the late ’70s," says Ollie Evans of vintage store Too Hot Limited. "The first incarnations of the football casuals were called the Perry Boys due to their polos. As the look developed and evolved into casual culture proper, with one-upmanship over more expensive and exclusive sportswear, tennis wear became the must-have for young football-going lads."

The shirts that started as a reaction to tennis’ stuffy early days were now being worn by young people of all backgrounds reacting in a hundred different directions. In an interview alongside Perry years later, Lacoste said, "I made the shirt, and you made me a great compliment doing the same thing." The Englishman responded, "You made the back of it longer than the front — so between us, we revolutionized it, didn't we?"

Bjorn Borg vs. John McEnroe

Getty Images / All Sports / Steve Powell Getty Images / Steve Powell

After tennis style OG Arthur Ashe blazed a trail with his color combinations and on-court accessorizing through the ’60s and ’70s, a new breed of sartorially switched-on tennis star was about to break through. Bjorn Borg, a Swedish style maverick who won his first Grand Slam, the French Open, in 1974 aged just 18, sent shockwaves through the sport, stealing hearts with his daring, disco-inflected looks and long flowing locks.

When Borg won five Wimbledon titles in a row from 1976 to 1980, he did so wearing Diadora Borg Elite sneakers and a pinstripe Fila Settanta Mk1 polo shirt. Both products became massively sought-after by football casuals, as did Borg's Fila Settanta track tops, which he donned to collect his trophies.

Bjorn Borg wins Wimbledon, 1978 Getty Images / Fox Photos

Described as "the first rock star of tennis" by British newspaper The Telegraph, Borg was the style inspiration for the character Richie Tenenbaum in Wes Anderson's cult movie The Royal Tenenbaums. In 2017, Williams and adidas paid tribute to Borg's look with the Tennis Hu capsule, worn by German up-and-comer Alexander Zverev at that year's US Open.

Borg formed one of tennis' eternal rivalries with John McEnroe, an American known for his outlandish tantrums. They were called "Fire and Ice": Borg the ice-cool Scandinavian, McEnroe the incandescent brat.

The pair shared a penchant for slim-cut Italian tracksuits. Like Borg, McEnroe liked to take to the court in a zip-up jacket, but his were by Sergio Tacchini, the Italian tennis player's eponymous label and another that was adopted by the UK's football casuals. In 1978, however, McEnroe ditched Tacchini for Nike. The Swoosh tapped into McEnroe's rebellious attitude, launching a range of countercultural apparel and, most notably, the Air Trainer 1 sneaker, designed by the legendary Tinker Hatfield.

John McEnroe wearing the Nike Air Trainer 1 Nike

"One of the most sought-after items on the terraces of the early ’80s was the Bjorn Borg Fila Settanta jacket, along with the Diadora Borg Elite trainer, the most expensive tennis shoe of its time," says Evans. "Then you had the adidas Ivan Lendl range, with its distinctive argyle print design, the iconic Sergio Tacchini track jackets worn by John McEnroe pre-Nike partnership, and the most expensive of the lot, the Cerruti 1881 pieces worn by Jimmy Connors.

"All these items were mainstays of ’80s casuals culture, which has huge parallels with today’s world of streetwear and the quest for the most exclusive, expensive, and hard-to-get-hold-of pieces."

Andre Agassi vs. Pete Sampras

Getty Images / ALLSPORT / Al Bello Getty Images / ALLSPORT / Clive Brunskill

If the ’70s and ’80s were foundational years for modern tennis style, the ’90s was when it exploded. Enter Nike, Pete Sampras, and Andre Agassi.

Agassi was unlike most tennis players — mainly because he hated the sport. Forced into playing by his disciplinarian father, who had represented Iran as a boxer at the 1948 and 1952 Olympics, Agassi was a child prodigy whose talents eventually saw him uprooted from the Las Vegas desert to Nick Bollettieri's famed tennis school in Florida. He rebelled against his new school by drinking, smoking pot, and getting piercings and crazy haircuts, eventually convincing Bollettieri to let him ditch the academic aspect of his stay at the age of 14.

Having signed with Nike at 16, the upstart became known for his lurid outfits, famously turning up to the 1990 French Open in faded black denim shorts over "hot lava" cycling shorts. Such was his distaste for tennis' conservatism, he refused to play at Wimbledon between 1988 and 1990 because of its all-white dress code.

Andre Agassi, 1991 Getty Images / John Russell

Nike embraced its wild child, giving Agassi with his own line, Challenge Court, which was marketed to the Beavis and Butt-Head generation with the slogan "Tennis sucks" and a skull and crossed-rackets motif. Footwear-wise, Hatfield eschewed plain low-tops, kitting Agassi out in the bold Air Tech Challenge. "Look at them," said Agassi of the kicks. "They look like they’re going 80mph, and they’re just standing still."

Nike Challenge Court tracksuit TOO HOT LIMITED Nike Challenge Court tracksuit TOO HOT LIMITED Nike Challenge Court shorts TOO HOT LIMITED Nike Challenge Court polo TOO HOT LIMITED Nike Challenge Court polo TOO HOT LIMITED

"Agassi made a very old-fashioned sport into something fresh and exciting," says Evans.

"You also have to remember that this was the early ’90s and rave was huge in the UK, so this new Nike range really caught the public imagination and crossed over massively. I had a pair of the Challenge Court Huaraches that Agassi wore and they definitely transcended the role of tennis shoe into streetwear. You’d see people wearing them who clearly had never been near a tennis court in their life."

Like with Lacoste and Perry, Borg and McEnroe, if Agassi was the brash, neon-clad extrovert, Sampras was his quiet, considered antithesis, obsessed with inner-discipline to the point many interpreted him as bland. While Nike went buck wild with Agassi's outfits, with looks inspired by pirates and skateboarding, it went in the opposite direction with Sampras. After tempting him from Sergio Tacchini in 1993, Nike transformed its Supreme Court line — fronted by Bollettieri alumnus Jim Courier — into the NikeCourt line, with Pistol Pete its poster boy.

Sampras defeats Boris Becker to win Wimbledon 1995 Getty Images / All Sports / Steve Powell

The clothing's more understated, slightly middle-aged sensibility reflected the serve-and-volley specialist's more staid approach, a minimalist yin to Agassi and Challenge Court's maximalist yang. At Wimbledon in 1994, fresh from signing a rumored $15 million three-year deal with the Swoosh, Sampras took to the court at SW19 wearing a pair of baggy khaki shorts, causing a shock out of step with Sampras' reputation for dullness. An AdAge report from the time said the shorts were "based on his beach-style practice wear." Sampras, understated as ever, remarked, "I am not much of a fashion consultant, but they are different and they are comfortable."

Almost as iconic as NikeCourt's Swoosh-on-a-tennis-court logo, which would become synonymous with Sampras, were the Hatfield-designed Oscillate sneakers on the 14-time Grand Slam winner's feet. However, the stuck-in-his-ways Sampras initially refused to try them on, with Hatfield only getting him to test out the Oscillates by offering a game of pick-up basketball and tossing him a pair. Sampras never looked back, wearing Oscillates for the next seven years.

The Nike Air Oscillate Nike

“It was a great time for American tennis," said Sampras of his rivalry with Agassi. "We were one and two in the world. Everything clicked marketing-wise and we sort of transcended the sport." For Nike, it was good preparation for what came next.

Roger Federer vs. Rafael Nadal

Getty Images / Clive Brunskill Getty Images / AFP / ADRIAN DENNIS

It might be difficult to believe, but Roger Federer wasn't always known for his ice-cold urbanity. As a junior, the Swiss struggled with his temper and was prone to on-court meltdowns and unhinged bouts of racket-smashing. After signing with Nike in 1997, he quickly rose through the junior ranks, doing so while sporting a peroxide haircut and boyish grin more NSYNC than "RF."

In 2001, aged 19, the now-ponytailed prodigy announced his arrival by knocking out champion Pete Sampras in five sets in the fourth round of Wimbledon, going on to lift the trophy two years later.

Federer wins his first Wimbledon, 2003 Getty Images / Alex Livesey

As Federer filed the rough edges from his game, it became apparent we were seeing something special. Critics gushed about his on-court elegance, Federer's grace leading some to judge him in terms of artistry rather than sport. “It is becoming increasingly apparent that Roger Federer was Leonardo da Vinci in a previous life,” wrote The Times of London's Simon Barnes in 2005. The late author David Foster Wallace, a former tennis junior himself, went one step further in 2006, writing that watching Federer live was a "religious experience" in an essay for The New York Times. Soon the question wasn't whether he was the best of his era, but of any.

Federer had ascended to sporting royalty, befriending not just the Arnault family, but Anna Wintour, whom he credits with honing his regal off-court image. On it, Nike had followed suit, dressing the maestro in immaculately tailored polo shirts and color-coordinated sneakers and sweatbands. Arguably his slickest moment came at the 2007 US Open, which he won in a murdered-out ensemble that led fans to dub him "Darth Federer."

Federer at the U.S. Open, 2007 Getty Images / Chris McGrath

At Wimbledon, however, some of Federer's ’fits bordered on parody, with Nike perhaps taking the aristocracy vibe too far by decking him out in a white blazer complete with gilded crest on the breast pocket in 2006. It was the first of a number of outlandish gold-on-white retro looks Federer donned at SW19 and a nod to the tournament's stuffier early days.

If Federer was Nike's da Vinci, Rafael Nadal was its Michaelangelo. Just as Michelangelo hewed marble into transcendental sculptures, Nadal's brilliance was honed on the dirty clay courts of Spain. Like the two renaissance men, Federer and Nadal formed an era-defining rivalry, a contrast of styles that came right down to the clothes on their back.

Whereas Federer's game was all grace and fluidity, Nadal was power-based, a grunting warrior who could run down the court, digging into every sinew and muscle, and blasting opponents into submission. Unlike Federer's country club chic, the Mallorcan donned capris and sleeveless shirts that exposed his superhuman biceps.

Nadal rocking his quintessential look, Indian Wells 2008 Getty Images / Matthew Stockman

All good things come to an end, though, and Nadal would eventually trade in his sleeveless tops for T-shirts and the pirate shorts for a more traditional inseam. The reason? Age. "They were very comfortable, but not for my age," Nadal told InStyle in 2017. "When I was 18, 19, 20, they were okay. I decided to change up the style in 2009. You never know what can happen in the future, but playing again with those long pants is not going to happen. I’m too old for that.” True to his word, the pants never returned — but the sleeveless look was back at this year's Australian Open.

Nadal in sleeves at the 2017 U.S. Open Getty Images / Michael Heiman

From Nike's perspective, by pitting the two as brains vs. brawn, mind vs. muscle, the consumer was forced to choose which they identified with best. For Federer, it deployed a gold logo using the player's "RF" initials (which the player hasn't been allowed to take with him to Uniqlo after moving this year), whereas Nadal was represented by a direct reference to his nickname: the "Raging Bull."

Neither Federer nor Nadal's apparel lines have had the same cultural impact as Lacoste, Perry, Borg, or Agassi, but both players' on-court sartorial style offered something totally different from their peers. More importantly, the pair dragged the sport to new levels of skill and athleticism in front of global audiences, making the clothes memorable by the achievements they were witness to. We know each player's look because we saw them in combat at the pinnacle of the game, fighting out arguably the greatest match ever: Wimbledon 2008's marathon final, which Nadal took in just under five hours.

Nike lost its monopoly on this rivalry when Federer was poached by Uniqlo in 2018. Still, both men are still going strong, and we wouldn't be surprised to see yet another titanic clash at this year's Open.

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For more tennis, peep Supreme's relationship with the sport here.