Welcome to the Madness! Voting is simple – pick the most stylish guy by clicking on their name in the match up – no login required. Feel free to share your bracket with us and sway a few votes in the comments below. So, who ya got for the 2017 Sweet Sixteen?

Ryan Gosling vs. Kevin Love

Ryan Gosling

The kind of guy that can pull off wearing a pre-ripped white tee or a never-ironed linen shirt without anyone batting an eyelash. You know the guy. Gosling just gets the core component of fashion: If you wear something with confidence, no one will question it.

Kevin Love

PSA: Guys look great in sweaters. Kevin Love got the memo, then went above and beyond with the sweater-under-a-suit combination. The kicker? He can dress up a pair of sneakers without looking like he forgot to pack a change of shoes in his gym bag.

Oscar Isaac vs. Michael Hainey

Oscar Isaac

Let’s hear it for the boys…who can dress their smaller frame while highlighting their personal style at the same time. Oscar Isaac can teach a masterclass in tailoring his clothes to fit his build from slim cut suits to t-shirts that aren’t too long.

Michael Hainey

I’ll be honest: After taking down Chance in the last round, Hainey better go all the way – and I wouldn’t be surprised if he did with his infallible classic style. Bonus point for his ever-voluminous hairstyle, right?

Mahershala Ali vs. Dwayne Johnson

Mahershala Ali

I’d imagine Mahershala looking just as polished pre-fame when becoming a working actor was the only goal. He’s the kind of guy that makes anything he’s wearing the thing to be wearing. Case and point: My reaction to his longline shirt was definitely more, “huh..ok, ok” than “huuuh?.”

Dwayne Johnson

Can you smell what The Rock is cooking or what? Dwayne Johnson knows how to stir up an ordinary suit with patterns, unexpected texture, and a laidback vibe via a slightly unbuttoned dress shirt. If you want to try your hand at his style, add a brightly printed pocket square or a textured (suede, anyone?) jacket to your next outfit.

I Am Galla vs. Donald Glover

I Am Galla

I Am Galla can wear a cropped pant or head-to-toe monochrome look as if it was as breezy as basketball shorts and a plain tee. And by the look of this blogger’s life, he just might wear these dressed up outfits when he’s off-duty. What’s more? When it comes to grooming, this style pro knows how to rock a bit of scruff – and we’re very on board with that. 

Donald Glover

The steps to Childish Gambino’s heavy hitting (and accessible!) style: 1. Going bold with a floral camp collar shirt under an ankle-bearing suit, 2. Swapping chukkas for moccasins, 3. Opting for an invisible tie under a three-piece suit. We love that any guy can try these styling moves regardless of movie/music/television star budgets.

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Rami Malek vs. Tom Hiddleston

Rami Malek

Resident cool kid Rami Malek may be the dark horse in this year’s Men’s Style Madness. A willingness to mix color, pattern, and texture into every outfit gains him serious style points, but what earns him the slow clap is that he makes it seem like getting dressed is one of the fun activities that he gets to do every day.

Tom Hiddleston

Tom Hiddleston is a natural at making an all neutral outfit interesting. When the fit is as sharp as his, sometimes a pop of bright blue is all that’s necessary to make a simple suit feel seriously stylish. His commitment to head-to-toe tonals may only be rivaled by other Sweet Sixteener John Legend.

Idris Elba vs. Justin Timberlake

Idris Elba

Idris Elba’s style can be broken down like an algebra problem. Classic silhouettes + pop of unexpected color – unnecessary excess fabric = timeless perfection. His casual style is more experimental, and he makes a great case for shorts with high top sneakers.

Justin Timberlake

Justin definitely has an every-man style sensibility. He knows that a jacket can be a one-piece-wonder that can transform a shirt and pants into a “look,” and that a little bit effort can be more advantageous than a “go big or go home” mentality when it comes to style.

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HOW DO YOU JUDGE EACH CONTENDER’S STYLE? ACCESSIBILITY OR ADVENTURE?

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