The term “men’s tennis style” tends to conjure the classics: short shorts with silver waist tabs, white polo shirt with a discreet logo on the chest, and maybe a terry cloth headband with a navy or green cheat-line through the middle. It’s a look with its roots in the Victorian era, but plenty of places around the world still maintain this traditional image (one big example: Wimbledon, the London-based Slam, requires an all-white dress code).

But peer beyond the surface fuzz, and there’s far more nuance to on-court style. For decades, male tennis players have added their own stamps of flair and flourish to varying degrees, from René Lacoste’s pragmatism in the 1920s (more on him shortly) to Andre Agassi’s rebel-child jorts of the 1990s (more on him, too).

Arguably, while prior eras had their characters, the 2000s were when the diversification of men’s tennis style accelerated. “Since Roger Federer’s dabbling in the world of higher fashion, the floodgates for who gets to be interested in style have really opened in men’s tennis,” says Caitlin Thompson, founder and editor of the tennis lifestyle publication Racquet. “Looking past current brand partnerships—though Lorenzo Musetti for Bottega Veneta and Stefanos Tsitsipas in a Loro Piana cape are elite examples—we now have a larger group of players who feel like they can experiment with style in a more overt way.”

Below, our list of the best, most notable, and most standout men’s tennis style fixtures.

René Lacoste—oui, of the surname-eponymous, crocodile-emblazoned label currently repped by the likes of Novak Djokovic and Daniil Medvedev—broke the mold in the 1920s. Tired of the long-sleeve shirts and pleated trousers that had until then been the men’s tennis norm, he shortened his sleeves into what would ultimately become the iconic Lacoste polo shirt as we know it today.

Arthur Ashe, for whom the Billie Jean King USTA National Tennis Center’s marquee court is named (and on which the US Open’s flagship matches are held), had fantastic tennis style. He hewed to its established tenets, yes, but he added just the right amount of cool-eccentric elements, like dashes of color and taking to the court in his horn-rimmed eyeglasses. (He did not have specialty eyewear made for competition.)

Björn Borg’s tennis aesthetic was flashy and high wattage in all the right ways. His fitted Fila jackets, headbands that held back his shoulder-length hair, gold chain necklace, and signature Diadora sneakers all gelled together to give the impression of a sort of sporting rock star. Or a music video viking. Or both.

Results aside, John McEnroe will go down in history for both his on-court skill and his volatile temper. And he’d be OK with that; he brings his behavior up often in his current role as a commentator. But second to that is his style: Johnny Mac rocked color-blocked Italian tracksuits from Sergio Tacchini before transitioning to loud Nike kits in the mid-eighties. Also usually present: a colorful headband holding back his wild curls.

Firstly: Yannick Noah’s Le Coq Sportif striped polos are a tennis grail (seriously, if you find one on eBay, buy it). Add his dreadlocks and flourishes like the David Bowie tee he wore for his practice session at Roland Garros in 1983, and you get the stuff of effortless on-court style legend.

Gustavo Kuerten, or “Guga” as he’s most commonly known, had an on-court style that channeled his home country of Brazil. His drip was known for being as vibrant and easygoing as his disposition—Kuerten was so famous for his ever-present smile that fans nicknamed him the “human Labrador.”

Andre Agassi, tennis’ most famous enfant terrible, was the Dennis Rodman of the baseline. He wore everything from acid-washed denim shorts to a full mullet to a famed “pirate” look (replete with a bandanna and silver tight-hoop earrings). Being anti-establishment was Agassi’s thing; he has spoken about actively choosing to rebel against tennis’s stuffiness through his style.

Chang is a poster child of 1990s-era Reebok—an era of time-stamped graphics, looser-fit clothes, and pre-millennium swag that defined the brand’s aesthetic. Those graphics really were amazing.

Lleyton Hewitt is on this list for one thing and one thing only: nobody in professional men’s tennis has worn a backward cap better, nor with more swagger. It pretty much became the two-time Slam winner’s sartorial signature. We’ll see if his son Cruz, who competed in his first ATP Tour event this summer, follows suit.

Federer is known for having a classically beautiful tennis game, and this was mirrored in his poised and polished on-court style choices. He also knew the power of a changeup; at the 2007 US Open, Federer worked with Nike, his longtime sponsor before Uniqlo, on separate daytime and nighttime fits. His sleek, dark, nocturnal look earned him the nickname “Darth Federer.” Federer is also a darling of the fashion world, having attended and hosted Met Galas, collaborated with Oliver Peoples, and been dressed by everyone from Burberry to Gucci.

Rafael Nadal did not pioneer the sleeveless tee in tennis, though he absolutely popularized it in the 2000s. Combine his muscle-flaunting tops with his aughts-era “pirate” shorts—insane 18-inch inseam capris from Nike—and it all contributes to the man’s style icon status.

Grigor Dimitrov is actually not all that dissimilar from Federer; his tennis style has always been classic, and the broader fashion world has embraced him. But there is one difference: Dimitrov was an early adopter of Van Cleef & Arpels, the French jewelry house, and nowadays, as the player Reilly Opelka recently commented on Instagram, “the ATP tour has a Van Cleef addiction.”

In addition to working hard to match Agassi’s record for shenanigans, both on and off-court, Nick Kyrgios earned his place on this list for his blending of basketball and tennis cues. For a while, he wore proto-basketball jerseys over compression shirts during play, warmed up in Lakers and Celtics jerseys, and, most famously, wore his red Air Jordan 1 Lows at Wimbledon.

A Slam winner with spectacular form and showmanship, Alcaraz is often seen in hyper-saturated Nike kits, flexing his impressive physique. One big point worth mentioning here, too: he’s the present-day hair standout, too. Remember when he went platinum after winning the 2025 US Open? Now, he’s rocking flowing locks with a soccer-ish headband.

Reilly Opelka, currently ranked 142 in the world, is that rare tennis athlete who has openly and frequently expressed his deep interest in art and style. He brings it to the court, too, such as with custom Technifibre bags made in collaboration with Tim Van Leare Gallery. The collaboration has even extended to a racket, which is matched only by Naomi Osaka’s stick with custom artwork by Takashi Murakami.

Frances Tiafoe, who is now sponsored by lululemon, is often seen in boldly colored sleeveless looks. At the 2026 Australian Open, he wore a spray-paint motif with colors of the Sierra Leonean flag to honor his heritage. In Washington, D.C., a few weeks ago, he wore a maroon-and-yellow kit to pay homage to his favorite football team: the Washington Commanders (Tiafoe was raised just outside the US capital). Also: his ubiquitous, glinting-silver “BIG FOE” chain.

Lorenzo Musetti was mentioned at the jump, and he deserves a callback here: his Bottega Veneta alignment is the best high-fashion partnership in tennis. Jannik Sinner has Gucci, Alcaraz has Louis Vuitton, Jack Draper has Burberry, but the way Musetti carries BV feels like the most natural and synergistic fit.

Tomáš Macháč, currently ranked 62 in the world, has made a stir in the tennis world for pushing the limits of short shorts. He’s been lightly roasted by Tennis Twitter, but he cares not. A lot of leg is the Macháč M.O. (And, from a movement perspective, it makes sense.)