If you have trouble picking what to wear in the morning, imagine the pressure of stepping out as a celebrity. For the famous men among us, getting caught around town in a bad ‘fit can land you on just as many blogs as a good look will (and kick off a good ol’ fashioned Twitter roasting, too). So, hats off to these 12 famous faces, who’ve managed to navigate that sartorial minefield this year with style to spare. The musicians, actors, and Kardashian-adjacent figures on this list typically fall into one of two fashion camps: those who keep it low-key and relatable, like Donald Glover and Chance the Rapper, and those, like Jaden Smith and Young Thug, who swing for the fences every time. Whether they’re going big or staying streamlined, each of these guys offers a lesson in dressing like they came to win in 2016.
12. Chance The Rapper
Photos by Dimitrios Kambouris / Getty Images; Neilson Barnard / Getty Images
Chance The Rapper, along with Donald Glover, is one of the great low-key style champs of 2016. He is frequently spotted in what most would call workwear style classics: overalls, suspenders, varsity bombers, denim trucker jackets, crisp white tees, and his signature “3” baseball cap. The total effect is that of boyish charm with well-fitting staples, and the occasional monochromatic moment. Appropriately, his sneakers game—a rotation of Nike Foamposites, Air Force 1s, Air Max 1s—is just as laid back and legit. Chance’s style never takes center stage. There’s a pared back safety and consistency that we’d attribute to the birth of his daughter in late 2015, as well as the soul-baring lyrics of his third album, Coloring Book. He’s focusing on the bigger things, and in doing so, Chance is giving us young baby-daddy style at it’s finest. —Deidre Dyer
11. Donald Glover
Photos by Frederick M. Brown / Getty Images; David Crotty / Getty Images
Things Donald Glover Can Do That Your Fave Could Never:
5. Land a role in the new Star Wars movie the same year he debuted one of the most critically -acclaimed new shows on television, the same year he dropped a new album.
4. Rock a double-breasted suit, change into a black tee and jeans, and look equally assured in both.
3. Make trucker hats seem not-so-awful and 2016-appropriate.
2. Inspire rabid Reddit fandom centered solely on his affinity for Nike Cortez sneakers.
1. Claim a place as one of the best-dressed men of the year and a low-key style icon simply by not trying too hard.
- The Best Men’s Style Brands of 2016
- Donald Glover Is a Low-Key Style Icon
- How A$AP Rocky Became The Face of Luxury Fashion
10. The Weeknd
Photos by Lester Cohen / Getty Images; Noam Galai / Getty Images
You know you’ve undergone an effective style reinvention when your new haircut outshines the panther riding shotgun in your McLaren. When The Weeknd released his video for “Starboy” in September, it served not only as the first taste of his new album of the same name, but also the first time that we got to see the Canadian singer’s new look in action, as he cruised down the freeway alongside his feline friend sans his signature towering hair. The Weeknd’s transformation extended to his clothes, too, although there the change was more subtle. He still sticks to an all-black-everything palette, but the names on the labels have been given an upgrade: Valentino, Saint Laurent, Dior, Gucci. Throw in emerging brands like LongJourneyand Amiri and a Puma deal, and—yes, I’m going to say it: Abel, you’re a motherfucking starboy. —Steve Dool
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9. Frank Ocean
Photos by Cheriss May / Getty Images; Josiah Kamau / Getty Images
Frank Ocean spent the majority of the year largely out of the spotlight. While fans were feverishly awaiting his second album, he opted to drop a Calvin Klein campaign instead. This was the first that fans had seen of Ocean in long time: shirtless in his signature striped bandana and his Calvins, defiantly stating that he pushed back his record. With the eventual release of his dual albums Endless and Blonde, he came back ready to play with his image. In the visuals that accompany Blonde, he continues to rock the camouflage army jackets and skater boy stapes that’s he’s known for, but also he dons a studded Balmain jumpsuit and heavy duty Nascar-style racer gear.
All of this goes to show that Ocean is a man who does things—album releases, recording contracts, personal style—on his own terms. This theory is one that culminates in his legendary choice of attire for President Barack Obama’s final State Dinner at the White House this past fall. Ocean turned up in the requisite natty navy blue, but paired it with checkered Vans Slip Ons. When asked about his footwear of choice, Ocean had this to say: “You can’t think—you just gotta do things.” —Deidre Dyer
8. Justin Bieber
Photos by Marc Piasecki / Getty Images; Kevin Mazur / Getty Images
The year of Purpose Bieber had all sorts of ups and downs, highs and lows, and many things that left us wondering: Does this dude really give a shit anymore? Or does he give too much of a shit. He literally and figuratively held no punches back, seemingly tired of being the person everyone wanted him to be. It seems superficial to point out that 2016 was arguably Bieber’s most stylish year ever as he worked his way through other obstacles in his personal and professional lives. But, in a turbulent period for him, the individual style he’s cultivated became one of the most consistent aspects of his public persona.
Bieber got fits off all year, frequently keeping it ultra-casual, traveling around the globe on tour as an ambassador for Los Angeles streetwear connoisseur-dom in Supreme, Gosha Rubchinskiy, and Off-White. It’s his relationship with Fear of God designer Jerry Lorenzo that truly had him flourishing, as he teamed up with the L.A. native for his own personal custom pieces and tour merch. While he’s still searching for perfection, he is beginning to truly understand the purpose of individual style. —Nick Grant
7. Rami Malek
Photos by Evans Vestal Ward / Getty Images; Valerie Macon / AFP / Getty Images
I know precious little about Rami Malek. I’m aware that he’s the Emmy-winning star of Mr. Robot —a show I have not watched. I also know that Malek wears a suit like he was born in one, has great taste in bomber jackets, isn’t afraid to throw on some prints and patterns when the occasion calls for it, and graduated from high school with erstwhile star of The OC, Rachel Bilson. I’ll confess that last fact came to me via Wikipedia. The other statements, though, are easily proven time and time again whenever Malek makes a press appearance or walks a red carpet. He hasn’t had many notable style missteps as his celebrity has grown, which, as many other young actors can attest, is a very rare feat. So, if there’s one thing you need to know about Malek, it’s that he will likely continue to be one to watch from a style perspective for the foreseeable future. And if there are two things to know, it’s that he also went to high school with Kirsten Dunst (Wikipedia again). —Steve Dool
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6. Gucci Mane
Photos by Paras Griffin / Getty Images; Prince Williams / Getty Images
Gucci Mane was released from jail this past May, and nothing’s been the same since. In six months, the Atlanta rap veteran has already dropped two albums (Everybody’s Looking and Woptopber), several singles and collaborations, and a mixtape with Lil Uzi Vert (1017 vs. The World). Music aside, the post-prison Gucci emerged as a new Gucci—sober, fit, and everyone’s favorite style star. He still has his signature oversized sunglasses, but clothes fit him better now and he’s taking plenty of risks. In fact, he performed at the BET Hip-Hop Awards in a rich, black fur coat with fur Fendi accessories hanging off of it.
None of this was by accident though. Shun Melson, Gucci’s longtime stylist, told us in an interview that she and the rapper worked together to build his new wardrobe while he was still locked up. Now, that’s what you call being proactive. Gucci appeared on Vogue talking about the high-fashion label Gucci. He released a sock collaboration with Stance just last week. He also set up Twitter and Instagram accounts for his Santa chain. What else do we need to tell you? Get this man a crown. —Karizza Sanchez
5. Scott Disick
Photos by Bauer-Griffin / Getty Images; Denise Truscello / Getty Images
Is Scott Disick the most unexpected entry on this list? Maybe, if you haven’t been paying attention to the style evolution of the man best known as the father of Kourtney Kardashian’s three kids. As we told you in back in May, Disick has been slowly and steadily stepping up his fashion game, phasing out the cravats and madras shorts of his past for bombers, ripped denim, and oversized hoodies. In other words, he’s dressing like a real person who lives in the present day, and not someone from an American Psycho-era fantasy of Manhattan who long ago crossed over into self-parody. Sure, he’s not breaking new ground—you could argue that he’s simply dressing like his sort-of-brother-in-law Kanye West—but what makes Disick stand out isn’t only how far he’s come, but how effortlessly he’s managed a complete style overhaul. He makes following in the footsteps of others look good and look natural. —Steve Dool
4. Jaden Smith
Photos by Stefanie Keenan / Getty Images; Jon Kopaloff / Getty Images
It’s safe to say that no one has more fun getting dressed than Jaden Smith. At just 18 years of age, Smith has mastered the art of IDGAF style. This statement is in no way a diss or a takedown. Rather, it’s praise for the playfulness and spontaneity that he embodies every time he steps out the door. This year alone, he rocked frilly blouses on the cover of NYLON, donned a skirt and blue nail polish for a highbrow Louis Vuitton campaign, and ran around the streets of NYC and LA in the gnarliest graphic tees and bomber jackets—all while holding a container of his own brand of water as if it were a phone. Not to be forgotten was the peak IDGAF moment when he used three Cartier Love Rings as beads to hold his locs together; gold rings that are valued at $1650 a piece. Just when we thought that he couldn’t top rocking a Batman costume to Kanye’s wedding, Jaden has shown that youthful wackiness just gets more refined and eccentric with age. Can’t wait to see what he’s dressing like at 25. —Deidre Dyer
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3. Rae Sremmurd
Photos by Prince Williams / Getty Images; Johnny Nunez / Getty Images
2016 has been a huge year for Rae Sremmurd. In August, they released their sophomore album, SremmLife 2. Earlier this month, their single “Black Beatles” became the soundtrack to the Mannequin Challenge and, as a result, their first Hot 100 No. 1 hit. The boys are now undisputably rock stars, and they definitely dress like it. Gucci pink mink fur coats, Gucci ski goggles, studded leather jackets, embroidered Gucci jeans, and their favorite look: going shirtless. —Karizza Sanchez
2. Young Thug
Photos by Paras Griffin / Getty Images; Prince Williams / Getty Images
Thug wears risky, sometimes borderline insane outfits, but there’s a genius to all of it. What else would you call the cover of his No, My Name is Jeffrey mixtape, on which he wears a ruffled gown? What’s most impressive about him is that, much like Iman Shumpert, he doesn’t have a stylist. So, while your *other* celebrity style icons are just throwing on a jacket someone told them to wear, Thug is like, “Nah. I’ll rock with this gender-bending dress that I like.” Not to mention that he’s the one adjusting a model’s outfit on the runway. Thug is a style star, and his Calvin Klein campaign, in which he was rocking the women’s collection, is my favorite thing of 2016. You can quote me on that. —Karizza Sanchez
1. ASAP Rocky
Photos by Jason LaVeris / Getty Images; Brian Ach / Getty Images
2016 can be marked as the year that ASAP Rocky completed his ascension from streetwear star to bona fide high fashion habitué. With the help of consistently killer front row style—see his Gucci Resort 2017 look—and his appointment as the new face of Dior Homme, Rocky became the “Fashion Killa” that he rapped about years ago. What’s been truly great about Rocky’s rise is a few things that have remained true; he hasn’t turned his back on any of the hallmarks that made him him. Rocky is still very Harlem jiggy, as evidenced by the floor-length mink he rocked at the Yeezy Season Three presentation. With his nostalgic Guess Jeans collaboration, he’s shown that he hasn’t forgotten the great streetwear brands of his youth. And no one can rock a classic ’90s style moment quite like him: white t-shirt tucked into light blue jeans, casually cinched with a belt, and topped with a black sport coat. Rocky is the rarest of style dudes; a man who can naturally embody the past and present with the ease of a furry Gucci mule. —Deidre Dyer