40 Best-Dressed Celebrities 2021 – 2021 Best Men’s Celebrity Style Leave a comment


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The way we dress now is changing. Old codes are out the window, new ones are still being written, and all around, it’s clear that there’s no one way to do things anymore. That’s great news! It means we’re free to forge our own paths, and maybe even get a little freaky with it. But it’s also, perhaps, a little overwhelming.

So, when things are in flux and the answers aren’t easy to come by, what’s a guy to do? First things first, take a look at the folks on this list, a compendium of the best-dressed celebrities on the planet right now. Here, you’ll find everything from new-bohemian badassery and statement-making, capital-“F” fashion to easygoing, everyday outfits that even the most low-key dresser can appreciate. Take a page from any of these guys’ style handbooks—or, hell, take one from each of ’em—and you’ll be in good shape. Here’s to a very well-dressed 2021.

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Jeremy O. Harris
Playwright, 31

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Does anyone have more fun getting dressed than Jeremy O. Harris? It isn’t easy to rock culottes and a coral clutch and make it look like a natural pairing. When he’s not overturning conventional notions of how a “serious writer” (or, hell, any man) should dress, the playwright is nestled at home in sweats, sometimes of his own design, proving you don’t have to throw on the wildest thing in your closet to dress up.

Black Cursive Text Lounge Pants

SSENSE WORKS
ssense.com

$200.00


the real og

Dapper Dan
Fashion designer, 76

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The man who helped define early hip-hop style is still at it, outfitting celebs in his Harlem atelier (run in collaboration with Gucci) while looking just as good as—and, let’s face it, sometimes even better than—his A-list clientele. If you want to see what dressing for the occasion while maintaining your signature swagger looks like, look no further than Dap.


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Justin Theroux
Actor, 49

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The past couple years have seen an upending of the tight, tailored approach to dressing that dominated the decade prior. Unless you’re Justin Theroux, who still wears skinny jeans and trim blazers like it’s 2011—and looks damn good doing it. This is a guy who knows what works for him, dialed it in years ago, and is absolutely intent on sticking with it. It’s something to aspire to.

Suede Chelsea Boots

Common Projects
endclothing.com

$515.00


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LeBron James
Basketball player, 36

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Although LeBron James came to style fame for his impeccable tailored fits—check out his Thom Browne short suit from 2018—he’s used that spotlight to amplify his political beliefs at a time when one can’t not take a stand. King James’s statement shirts do just that and happen to look really rad while they’re doing it.

Tears, Flags & Caskets Tee

Denim Tears
denimtears.com

$50.00


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Harry Styles
Musician, 27

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In a word: delightful. That’s how we’d describe Harry Styles’s, er, style. Not only because his flared trousers, fantastical knitwear, and all-around panache make music and fashion fans around the world smile at the sight of him—though that’s true, too—but also because he looks like he’s having so much fun with his clothes (and nails, and everything else). Achieve even half of that enjoyment level yourself and you’re on the right track.


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Jamal Adams
Football player, 25

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In a league that’s increasingly full of peacocks (look out, NBA), Jamal Adams stands out by being one of the few who seem like they’re wearing the clothes and not vice versa. It’s the art of taking something like this Jaws statement sweater by Raf Simons for Calvin Klein 205W39NYC—not to mention those Fragment x Air Jordan 3’s—and weaving it into a look that feels easy and approachable.

Bouclé Crewneck Sweater

Topman
nordstrom.com

$37.50


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A$AP Nast
Musician, 30

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It takes a lot to stand out in a group of friends as formidably dressed as the A$AP Mob, but self-professed Prada fiend A$AP Nast makes it seem easy. His look isn’t readily replicable for everyone following at home, but to start, try pairing something as mundane as a parka with, say, a roomy pair of black dress pants and a sleek cross-body bag. It’s this high-low mix that makes Nast such an expert-level dresser, and it’s this exact anything-goes approach that you should bear in mind when getting dressed this year.

Logo Print Shirt

Prada
farfetch.com

$655.00


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Steve Lacy
Musician, 22

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How many bona fide celebrities have a separate Instagram account dedicated solely to documenting the sheer enormousness of their everyday wardrobe? We know of only one: Steve Lacy. The man can wear anything with a total lack of pretension. To channel his energy, throw on those things you bought and then never wore, no matter how funky, and immediately try to forget you’re wearing them. (A fringed knit vest and a lacy white top might be a bit much to bite off right from the start, but you get the idea.)

Saint Jones High-Neck Knit Cardigan

Wales Bonner
matchesfashion.com

$550.00


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Jerry Lorenzo
Designer, 43

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In 2020, Jerry Lorenzo emerged as a signature voice in American men’s wear, partnering with the tailoring whizzes at Zegna and churning out a Fear of God collection chock-full of strong-shouldered suiting and slouchy sweats. No one wears the brand better than Lorenzo himself. To imitate his elevated laid-back cool, just remind yourself that your swankiest sport coat need not be treated any more preciously than your trustiest sweatpants. The rest will come naturally.

Brushed Knit Hoodie

Fear of God
ssense.com

$935.00


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Travis Scott
Musician, 28

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Over the course of the past few years, Travis Scott transformed himself into a defining force behind streetwear’s merger with the luxury mainstream. (Want proof? Just look at how he mixes archival Raf Simons with Rick Owens sweatpants and sandals from the venerated Japanese brand Visvim.) None of it should work, but it does—in part because Scott is a global superstar, sure, but mostly because he has an intuitive grasp of the connective threads between the pieces. Remember: The sundry items in your wardrobe can still sing together in beautiful harmony out and about in the real world, no matter how little they appear to have in common hanging in your closet.


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David Byrne
Musician, 68

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David Byrne’s style is an open-and-shut case of finding a look and perfecting it over the years. For Byrne, a suit has never been a formal, stiff thing, even when it famously had exaggerated shoulders. Instead, it’s the ultimate blank canvas at any age. And in his book there’s always a little wiggle room for a fun piece like Doc Marten Mary Janes or a Utilikilt.

Light Grey Havana Jacket

Suitsupply
suitsupply.com

$399.00


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Offset
Musician, 29

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He can do tailoring and streetwear with the best of ’em, but Offset’s most impressive skill is his ability to wear the swerviest stuff out there—wacky prints and colors and patterns from the likes of cult Japanese label Kapital—and look entirely at home in it. He proves that anything is possible if you just give it a shot.

Intarsia Fair Isle Wool-Blend Sweater

KAPITAL
mrporter.com

$680.00


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Dev Hynes
Musician, 35

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Dev Hynes dresses like the cooler older cousin you never had. The crooner has a penchant for softly tailored, gently elegant looks that are as deftly executed as any of his funkiest bops. The next time you reach for your go-to all-black outfit (always a good look, FYI), consider making like Hynes by playing with textures and shapes you might normally avoid. It’s the elevation of the otherwise mundane to the delightfully thrilling that lends Hynes’s style its deeply personal touch.

Wool Jax Beret

Kangol
freepeople.com

$65.00


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The men who defined the style of the decade


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John Mayer
Musician, 43

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John Mayer is the kind of guy who can do workwear, streetwear, or tailoring and make you believe it. It’s proof you can be a style student who won’t pick a major but gets an A in every class. The lesson: Try it all, because at some point, something will feel just right.

Social Sculpture Handyman Damaged Shirt

Visvim
endclothing.com

$769.00


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Brad Pitt
Actor, 57

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Brad Pitt’s great power is that he’s too damn handsome to look bad in (checks notes), yep, anything. But with that power comes responsibility, and whether he’s ripping a duke in an overshirt, ripped jeans, and slip-ons on the back of a food-delivery truck or draped in Brioni on the Cannes red carpet, Pitt hasn’t phoned it in since (checks notes again), yep, ever. Yet, again, it’d be hard to tell if he did. Want to steal a dose of Pitt’s style? Build up a collection of vintage tees and exhaust yourself pairing them with everything from workwear to suits.

Jersey Rev. Check Shirt

Portuguese Flannel
huckberry.com

$81.98


the tailoring trailblazer

Kristen Stewart
Actor, 30

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In an era when men have never had more choice in how to express themselves with clothing, it takes a woman like K-Stew to remind us (regularly) that the best men’s clothes are somewhat eternal and that a simple casual uniform will still go a long way. Feted for borrowing vibes, from Thom Browne’s tailoring to skater chic—and doing it better than we do—she makes it clear that style is as much about how you wear it as what it looks like.

Grosgrain-Trimmed Cotton-Oxford Shirt

Thom Browne
mrporter.com

$450.00


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Anderson .Paak
Musician, 35

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From album names like Ventura, Venice, and Malibu to a recent team-up with Vans, Anderson .Paak has always repped for southern California and his hometown of Oxnard (also an album title). Sonically, that means music that encompasses everything from funk to hip-hop to soul. Stylistically, it means an easygoing approach to getting dressed filled with bright colors and bold prints. If it’s always sunny and 72 degrees in your head, you might as well dress like it, too.

Venice Bucket Hat

Vans x Anderson .Paak
sneakersnstuff.com

$49.00


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BTS
Musicians, 23 to 28

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There’s much to admire about BTS—tireless work ethic, progressive stances on masculinity, status as the world’s most popular band—but man, the outfits. Whether they’re in hoodies or overcoats, the guys usually have one bold element and a touch of artful slouchiness but always exude absolute comfort, as if they were perpetually about to board a Gulfstream to the world’s best party. It’s a reminder that if you feel good in your clothes, you’ll look good, too.

Double-Breasted Relaxed Fit Coat


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Dan Levy
Actor, 37

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The man who should be the next Clark Kent, and not just because of the (perfect) specs. Dan Levy’s got a superhuman ability to play the whole style spectrum. From stripped-down luxury (see the Gucci- sweater-anchored fit here) to an Emmys- sweeping kilt, his approach is what personal style is all about: willingness. We’ll bow to that.

Cashmere Cable-Knit V-neck Cricket Sweater


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Timothée Chalamet
Actor, 25

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You don’t have to go full space-age Don Johnson (we mean that as a compliment, of course) to channel Timothée Chalamet’s Haider Ackermann–blessed look at the 2019 Venice Film Festival. The takeaway is that you can still push your personal boundaries without crossing into the indecipherable, and don’t be scared to push up those jacket sleeves.

Screen-Printed Loopback Hoodie

Celine Homme
mrporter.com

$690.00


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Lenny Kravitz
Musician, 56

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Skipping six buttons and tying your shirttails in a tight knot above your belt buckle shouldn’t look good on anyone. On Lenny Kravitz, it looks fantastic. Can we all pull off the kinds of looks he can? Nope! But we should absolutely channel the sort of confidence and creativity that lets him not just break the style rules but also render them entirely moot.

Bone Button Western Shirt

Flint and Tinder
huckberry.com

$128.00


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Chris Gibbs
Owner, Union Los Angeles

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As the owner of the West Coast’s hottest clothing store, Chris Gibbs could easily look like a walking ad for rare- clothing culture. That he doesn’t is a testament to his personal sense of style, one that never lets the desirability of a piece get out in front of him. He’s a contemporary manifestation of that ancient quote from Sir Hardy Amies: “A man should look as if he’s bought his clothes with intelligence, put them on with care, and then forgotten all about them.”

Union Denim

Union L.A.
unionlosangeles.com

$330.00


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Blondey McCoy
Artist, 24

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The flash of Burberry tartan and one type of camo isn’t enough for the cheeky, prep-inflected skate-style god who ups the ante to punkish perfection. Blondey McCoy’s choices offer a lesson: If you’re putting together a busy fit, go all the way busy, then dial it back one notch.

Iconic Button-Through Vertical Stripe Polo

Ben Sherman
bensherman.com, $109.00


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Tyler, the Creator
Musician, 29

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Copying Tyler, the Creator’s knit-heavy take on neo-prep calls for raiding your grandpa’s closet and then imbuing whatever you find with a serious dose of cooler-than-thou attitude. It’s the little tics—the off-kilter cap, the scarf casually shoved into his pocket—that really make his style one of a kind. If the devil’s in the details, Tyler’s style is a reminder to find a few distinct to you and incorporate them into every outfit, no matter where you’re headed.

Wool Cardigan

MR P.
mrporter.com

$330.00


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Bad Bunny
Musician, 26

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Whether he’s performing in a pleated black skirt or in 50 shades of fleece-lined neon yellow, Bad Bunny understands the power the right outfit has to make a serious statement—particularly when you’re one of the biggest musicians in the world. Never be afraid of going big. Feeling that bright-orange parka? Go for it, man. If you’re having fun, who cares what anyone else thinks?

Italia Columns Silk Shirt

Casablanca
endclothing.com

$659.00


A version of this story appeared in the March 2021 issue of Esquire magazine

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