5 most stylish men in the history of Tennis

When you think of tennis, you don’t just think of killer serves and grueling baseline rallies. You think of the style. The crisp whites, the immaculate tailoring, and that effortless "old money" vibe that the internet is suddenly obsessed with trying to replicate.

Long before quiet luxury became the buzziest trend in fashion, the tennis court was the ultimate menswear runway. From the invention of the cotton polo to modern luxury watches flashing under the stadium lights, the sport has always been a place to serve serious looks.

So, who actually did it best?

Let’s break down the five men who didn't just play the game—they completely redefined court elegance.

Before Lacoste came along in the 1920s, tennis players were basically suffocating in stiff button-down shirts and neckties. Imagine trying to hit a backhand in that kind of getup.

René changed the game entirely by inventing the short-sleeved cotton piqué polo. And yes, he slapped his now-iconic crocodile emblem right on the chest.

He didn’t just wear the country club aesthetic; he essentially drafted the blueprint for it.

Today, it is impossible to talk about preppy elegance without tipping your hat to the foundation he built.

Arthur Ashe was living proof that traditional dress codes don’t have to mean boring.

His on-court outfits were always ridiculously sharp. We're talking quintessential white shorts with perfectly pressed forward pleats and clean, no-nonsense polos.

But his off-court fits were just as legendary.

Ashe had this habit of throwing on a beautifully tailored blazer and a pair of square-frame glasses, making him look effortlessly refined at all times.

He was pulling off understated elegance way before fashion magazines even had a name for it.

Enter the 1970s.

The world was getting a little louder, and Björn Borg was the guy holding the microphone on the tennis court.

With his long blonde hair and signature striped sweatbands, he brought an undeniable rockstar edge to a sport that had historically been quite buttoned-up.

Borg put Fila Settanta track tops on the map. He managed to make vibrant, athletic gear look like high-end leisurewear.

If you’ve bought a vintage track jacket anytime in the last five years, you probably have him to thank.

You simply cannot talk about tennis fashion without bowing down to Roger Federer.

The man literally brought bespoke menswear back to Centre Court.

Remember when he used to walk out at Wimbledon in a tailored cream blazer, a cozy cardigan, or even a crisp vest? Pure class.

But Federer’s style goes way beyond his clothes—he has a serious eye for high-end horology.

As a longtime Rolex ambassador, he’s hoisted Grand Slam trophies wearing everything from a classic Datejust to a highly complicated Sky-Dweller.

He proved, once and for all, that peak athletic performance and luxury watchmaking belong together.

Fast forward to today, and Jannik Sinner is carrying the torch.

Literally carrying it, in a custom monogrammed Gucci duffel bag.

When he stepped onto the Wimbledon grass with that bag last year, he broke the traditional mold in the best way possible.

It was a bold move, but a beautifully sophisticated one.

It’s the perfect snapshot of modern luxury.

Sinner, who is also a Rolex ambassador and often spotted rocking a Submariner, has this incredible knack for balancing the strict, all-white dress codes of the sport with genuine, contemporary high-fashion statements.

Whether it’s a vintage track top or a statement duffel bag, these five icons prove that tennis will always be the most stylish sport on earth.

The game might change, but the fashion is timeless.