The Most Stylish Athletes of All Time
Throughout the history of sports, select superstars have made forays into film, music and fashion too. And with the respect to latter, in particular, certain athletes have managed to reach great heights.
Roger Federer, for example, has transformed the tennis wardrobe, substituting bandannas and warm-ups for cardigans and blazers.
And in a similar fashion (pun intended), Walt Frazier used the 1970s to bring style and flair to the hardwood, while Dwyane Wade has done the same thing for a new generation of ballers.
Finally, with a little help from his fashionable wife, Tom Brady has blurred the lines between gridiron and Gucci, cementing his status as one of the best-dressed men in the world.
With, then, these stylistic trendsetters in mind, we’ve sought to create an elite and comprehensive list, specifically spotlighting the most stylish athletes of all time.
So with complete disregard for gender, popularity and sport, we bring to you the 10 athletes most capable of walking the walk and the runway too!
Charlotte Casiraghi
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I’ll admit—I wasn’t all that familiar with Charlotte Casiraghi until I started doing a little research for this piece. Then again, I’m not exactly an equestrian enthusiast.
But if unlike me, you are, well, then you definitely know of Casiraghi as much for her sense of style as for her skill with a horse.
Of course, it’s not as if Casiraghi is exactly defying the odds.
After all, the 28-year-old has been blessed with beauty and—as the daughter of Caroline, Princess of Hanover and Monaco—wealth and power too.
As a result of it all, she is Gucci’s official equestrian ambassador and has special outfits designed by the company’s creative director, Frida Giannini, for each competition.
From riding events to royal balls, Casiraghi has endless opportunities to stun crowds, and according to Forbes’ Raquel Laneri, she rarely, if ever, fails to do so.
Cristiano Ronaldo
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Simply put, Cristiano Ronaldo tries as hard to look good away from the pitch as he does to score goals on it.
Of course, he’s managed to accomplish both with remarkable success.
For his efforts, GQ Magazine (h/t Eurosport.co.uk) named the renowned goalscorer one of the Top 20 most stylish men in 2015.
Ronaldo has really taken the whole fashion thing in stride (pun intended).
In 2006, he opened his own fashion boutique and, with unsurprising vanity, named it CR7 (a combination of his initials and jersey number). And since then, the Portuguese heartthrob has launched a line of premium shirts and shoes too.
Then again, you know a dude is seriously into fashion when he says things like this, per Contactmusic.com: “I wear the luxury styles, like the Oxford Brogue, with tailored trousers and a well fitted CR7 shirt. I love using color and designs that are vibrant.”
Dwyane Wade
3 of 10
People could argue that either LeBron James or Russell Westbrook belongs in this spot—and they wouldn’t sound crazy if they did so—but we simply couldn’t leave Dwyane Wade off our list.
After all, while many of the league’s younger players have since followed suit—such as James, Westbrook and Dwight Howard, for example—it was the 33-year-old Wade who pioneered the NBA’s current “fashion matters” movement, a fact that many have recognized.
And in doing so, he’s raised everyone’s game, starting a virtual “swag” war.
Just don’t tell Westbrook that we think Wade’s winning.
Of course, Wade doesn’t look so good without trying hard to look so good.
And not so surprisingly, all the effort has paid off.
The Miami Heat star has been a GQ centerfold, a featured interviewee and the main topic in plenty of the magazine’s other style-based convos.
Fittingly, Wade played an active role in New York’s very first Men’s Fashion Week last July, recently partnered with fashion’s innovative Naked Brand to help launch new campaigns and has his own line of bow ties.
And in 2014, Forbes’ Rachel Hennessey agreed with our analysis, naming the three-time NBA champion the champion of suits and ties too!
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Lindsey Vonn
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Fashion means so much to Lindsey Vonn—and she to fashion—that even while limping on crutches, the 30-year-old alpine skier walked the runway during 2014 Fashion Week.
And with full confidence in the superstar’s style, InStyle Magazine followed and featured Vonn as she readied for the 2015 ESPYs.
The world champion also had Anna Wintour—for those who don’t know, she’s editor-in-chief of American Vogue—dress her for the 2013 Met Gala, and Vonn regularly sits front row at high-profile fashion shows, making waves all the while.
Finally, in addition to all the fashion fanfare, Vonn has used her sense of style to do a little creative work as well, teaming up with Cynthia Rowley in 2014 to design her own ski helmets.
David Beckham
5 of 10
In a July 22, 2002, editorial for Salon.com, Mark Simpson—who, by the way, coined the term metrosexual—said the following with regard to David Beckham: “The captain of the England football squad is actually a screaming, shrieking, flaming, freaking metrosexual.”
And if a metrosexual is a man who supremely cares about the way he looks and then executes said look to perfection, well, then Simpson couldn’t have been more right.
The versatile Beckham can look sophisticated one moment and then rugged the next, and either way, he will never be confused for one who doesn’t care.
And his resume in the field of fashion is nearly as long as his on the pitch.
At GQ’s 2013 Men of the Year Awards, the British superstar was named the most Stylish Man of the Year. In 2015, the Telegraph’s Stephen Doig called him “Britain’s most stylish man.” And Jason Basmajian, the chief creative officer of Gieves and Hawkes, has referred to Beckham as a “menswear icon” (h/t Doig).
And with so much stylistic credibility, Beckham has wisely capitalized, becoming an in-demand spokesman and model as well as the owner of numerous fashion lines, including David Beckham Instinct, his own aftershave and fragrance brand.
Roger Federer
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When it comes to modern-day tennis, credit the great Roger Federer for bringing style to the courts.
Before the Swiss legend, fashion in tennis was a mere afterthought.
But now, the most stylish tennis player ever has made it both a personal and—thanks to endorsement deals with Nike and Rolex—a fiscal priority.
Before Roger, bandannas and baseball caps were customary.
Simply put, Fed’s RF brand has transformed the way style in tennis is perceived.
It’s no wonder Michael Jordan himself—the King of Shoe—recently sought out Federer to design a new sneaker, per Telegraph Sport.
Arnold Palmer
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In the 1960s, there was golf, and then there was Arnold Palmer. Sure, Jack Nicklaus and Gary Player were popular, but The King brought style and swag to a sport that was woefully devoid of both.
“I can’t recall a specific moment when I realized that people were emulating my style because it’s such a personal thing for everyone,” said Palmer, per Sharp’s Donnell Alexander. “But there definitely was a point early in my career once I started winning tournaments that I realized people were taking notice of me. Style is very important to me. That was true way before I became a professional and has been the case ever since.”
He appeared on GQ’s cover when the magazine spotlighted the 25 Coolest Athletes of All Time, and the blog Wonderslist referred to him as the most stylish athlete of all time.
Of course, with his personal style garnering so much widespread appeal, Arnie couldn’t help but open his own clothing line.
Though Nicklaus is the game’s winningest competitor and Tiger Woods its modern representation, no one ever knew fashion or flair, clothes and cool, quite like The King himself.
Serena Williams
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The sport of women’s tennis is well-represented when it comes to fashion.
In fact, we could have easily mentioned Anna Kournikova or Maria Sharapova in this space.
Instead, we went with Serena Williams, who regularly makes bold fashion statements, both on and off the court.
Like no one before her, Serena will compete for Grand Slam titles and best-dressed awards all at the same time.
When it comes to her tennis gear, she’s thoughtful, inventive, daring and never boring or repetitive.
And away from the court, the fashionista and world No. 1 has launched her own clothing line, been featured during New York’s Fashion Week and has opened eyes and dropped jaws along the way.
Walt Frazier
9 of 10
Few could pull off felt fedoras, cashmere turtlenecks, velvet capes and oversized gold chains quite like Walt Clyde Frazier.
In fact, no one could.
Before Dwyane Wade, LeBron James and Russell Westbrook brought fashion back to basketball, Clyde "The Glide" owned both.
According to various GQ articles, Frazier was the original “NBA style icon” and a legend of NBA style, starring in fashion magazines and cruising in his Rolls-Royce all throughout the ‘70s.
And the excessive praise hardly stops there, as the magazine—not so surprisingly—also calls the Hall of Fame guard the most stylish NBA player ever!
Frazier’s gaudy gear recently inspired Vogue to feature his unique style and had the same effect on Grantland’s Wesley Morris, who in 2013 wrote an article titled “The Splendiferousness of Walt Frazier.”
Clyde—a nickname he earned away from ball as a result of his style—was the King of Cool on the court and never disappointed off it either.
Tom Brady
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While he may have a little help—he’s married to Brazilian fashion model Gisele Bundchen, for crying out loud—Tom Brady nonetheless ranks as one of the most fashionable men in all the world.
Want proof?
In 2012, Fox News Magazine named the New England Patriots signal-caller one of the 20 Best Dressed Men in Hollywood—including him with the likes of George Clooney, Will Smith, Johnny Depp and Brad Pitt—while Gentleman’s Playbook called Brady the Most Stylish Man of the Year.
Oh, and we should also mention that GQ considered the four-time champ one of the 25 Most Stylish Men in the World in 2010, and that Sports Illustrated thinks he’s a fashion icon.
But Brady sort of has to look good.
After all, the dude’s seen more red carpet than a Buckingham Palace vacuum!
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