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Home • Fashion

Celebrity Style: 50 Most Fashionable Men

Celebrity Style: 50 Most Fashionable Men
By Essence · Updated October 29, 2020
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Men of Style

Chris Bosh, Dwayne Wade and LeBron James look flawless in their tailored suits and lux footwear.

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Men of Style

Dwayne Johnson is a rock star when it comes to effortlessly cool ensembles like this.

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Men of Style

That permanent five-o’clock shadow of his always adds a touch of edge to Eric Benet’s classic style.

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Men of Style

Hill Harper always looks stunning in his smooth outfits.

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Men of Style

Djimon Honsou always pleases us with his smooth skin tone and equally smooth style.

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Men of Style

Presidential style is the only way to describe our President, Barack Obama, who always has a certain swag whether he’s holding meetings or playing golf.

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Men of Style

Drake has refined his style since his debut, evolving into a more mature, sophisticated artist.

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Men of Style

Carmelo Anthony always cuts a figure in a suit, but none better than the day of his “Full Court” wedding to his wife LaLa Vazquez.

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Men of Style

Jay-Z has graduated from football jerseys and fitted caps to sleek, sophisticated suits.

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Men of Style

Boris Kodjoe can do no wrong, especially when it comes to his wardrobe which is always as handsome as the man.

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Men of Style

Dipped in chocolate and swimming in style, it’s no surprise that actor/singer Tyrese made our list.

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Men of Style

Maxwell had us from hello with a silky voice — and an equally smooth wardrobe.

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Men of Style

Whether he is suited and booted or laid back with jeans and sneakers, Usher always oozes style.

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Men of Style

Even with one foot in a cast, there’s no denying Idris Elba’s stylish swag.

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Men of Style

What do we love about John Legend? That this man dresses just as well as he sings.

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Men of Style

There’s nothing Common about this artists sense of style.

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Men of Style

We continue to be enamored with Lenny Kravitz’s sophisticated, edgy cool vibe.

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Men of Style

It doesn’t get any smoother than Will Smith, who favors casual cardigans and tailored trousers.

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Men of Style

From those sexy eyes to that streetwise swagger, Terrence Howard barely needs any accessories to pull of his signature stylish suits.

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Men of Style

Fonsworth Bentley is known for his gentlemanly style, which continues to influence a generation of young men.

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Men of Style

Even when he covers up those legendary rippling abs, Tyson Beckford still excites us with his cool sense of style.

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Men of Style

No artist takes more chances with his songs and his style than fashion aficionado Kanye West, who has become a fan of tailored suits.

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Men of Style

Chad Ochocinco is known for more than that famous name: it’s his superstar style (you will rarely catch him without his signature shades) that also makes the ladies love him.

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Men of Style

Famed fashion editor Andre Leon Talley, here with Tyra Banks, always serves a stylish get up that is always head turning.

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Men of Style

Trey Songz has appeal that goes way beyond sex, the young crooner, is as stylish as they come in his signature suits and bow-ties.

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Men of Style

We have come to love his signature suits, but this shearling lined trench and not one, but two statement bags show that Mr. Foxx can switch things up.

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Men of Style

There’s something sleek and sexy about Taye Diggs’ laid back, urbane style of dressing.

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Men of Style

What more can we say about Shemar Moore’s smoldering, sexy style? We love him in whatever he wears, but casual suits like this are the best!

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Men of Style

will.i.am has always matched to the beat of his own drum when it comes to music and style. We love his eclectic look.

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Men of Style

With his stealth, sophisticated and urbane style Ryan Leslie continues to rate as a favorite of ours.

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Men of Style

Rick Fox, here with Amber Rose, picks pieces that are the epitome of ‘grown man style’ — well made, elegant and age appropriate.

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Men of Style

Ray J swings from corporate to streetwear in seconds. But no matter where on the spectrum he lands, he always has a stylish swag.

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Men of Style

From his Billionaire Boys Club line to collaborations with A Bathing Ape and Louis Vuitton, Pharrell Williams not only knows good clothes — he designs them.

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Men of Style

Prince: enough said.

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Men of Style

Who new Nick Cannon had such grown man style? We love his heavy rotation of buttoned-up looks!

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Men of Style

Theres a reason why designer Patrick Robinson has one of the best jobs in fashion as Creative Director for the GAP, he embodies sleek, simple style.

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Men of Style

The ultimate Urban Gentleman, Ne-Yo, knows how to look stylish in everything from a three piece suit to a casual ensemble like this one.

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Men of Style

With his handsome good looks almost anything looks good on actor, Morris Chestnut.

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Men of Style

Rapper Mos Def effortlessly blends his downtown vibe with uptown pieces like ties, vests and suits.

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Men of Style

Decades after bursting on the scene, Lionel Ritchie, still commands attention with his impeccable style of dress.

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Men of Style

A fit physique sure does a wardrobe good as LL Cool J consistently proves when he hits the red carpet.

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Men of Style

We wonder if a man ever looked as fine in a suite as Kobe Bryant does when he slips into a suit?

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Men of Style

LeBron James adds gentlemanly touches like fedora’s and leather strap watches to his off-the-court wardrobe.

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Men of Style

Up and coming artist Kid Cudi is exemplary, not only for his groundbreaking music, but his groundbreaking style.

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Men of Style

Off screen and on, Denzel Washington smolders with a swaggering, masculine style.

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Men of Style

Trendsetter and trailblazer that he is, it’s no surprise that when it comes to style Sean Combs is King.

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Men of Style

Chris Brown, whose star is back on the rise again, consistently rocks streetwear with a sophisticated edge.

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Men of Style

Blair Underwood always takes our breath away with his understated stylish swag.

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Men of Style

The rapper turned actor turned designer expresses his creativity in his wardrobe.

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Men of Style

Actor Isaiah Mustapha is best known for his shirt being off, but he’s just as easy on the eyes when he slips into his stylish duds.

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Men of Style

Dwayne Wade, here with girlfriend Gabriel Union, is as great a player on the court as he is a dress off of it.

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