Round 1 of 2017 Men's Style Madness: 7 VS 10 and 2 VS 15

Vote to close out the first week

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?

7 vs 10




Dev Patel

This laid-back Lion star hits the red carpet with the same effortless vibe as a trip to the grocery store – and about just as simple of a look. Patel keeps his style simple with basics like button downs, sweaters, and not-too-flashy formalwear.

Justin Trudeau

As far as elected-leader fashion goes, Trudeau is the leader we’ve been searching for. This Disney Prince of a Prime Minister impresses with suiting on par with his policies – from an attention-grabbing sweater and blazer combo to the mastery of the navy politician suit.




Dwayne Wade

Having met Dwayne Wade at the debut of his collaboration with The Tie Bar (did I name drop that smoothly enough? I think so..), I’m still impressed by how impeccably his clothes are tailored to his athletic frame. I love that he wears slim cuts and tries styles right off the runway without looking out of place.

Michael Hainey

This former GQ editor-at-large doesn’t need flashy trends or over-the-top Savile Row styling to turn heads when he walks into a meeting or poses for street style photographers. While we’re not exactly surprised that Hainey has discovered the power of pairing textures and patterns or the power of a good tailor, we’re still cheering on his classic aesthetic.




Cam Newton

Cam Newton’s accessory game is a bit rebellious and sure, he’s had a few fumbles (looking at you foxtail keychain), but his fashion risks usually pay off because of his attention to fit and color. The quarterback continues to play with styles and proportions – from preppy to trend driven – without losing his own sense of style.

J Balvin

Colombian singer J Balvin’s style has the same energetic vibe as his chart-topping music. Just ask our very own Intern Rita who met Balvin at this year’s Men’s Fashion Week. Whether in St.Laurent or Supreme, we love that his style is unique while properly fitting his frame.




Pedro Pascal

My swoon-worthy journey with Pascal started with Game of Thrones and continues to grow with every patterned suit or unbuttoned top button this guy throws at us. He keeps his grooming game as effortless as his red carpet style with tousled hair and red carpet combinations without superfluous flair.

Damian Lewis

I’ve seen exactly one episode of Billions and let me tell you: I get the Damian Lewis thing. You get the sense his on-screen confidence just might carry over into his real life, and that’s an enticing trait. As for his style? He nails the “off-duty actor” vibe with his affinity for scarves and casual-meets-dressy layered looks.

2 VS 15



Tom Hiddleston

Let’s first all agree to ignore the whole T.Swift publicity hiccup (and accompanying fashion foible). Whew, clean slate. Hiddleston always exudes English charm through his suited wins that he seems to wear as comfortably as a pair of sweats. It’s not an easy feat, but Loki gets it done.

Jim Chapman

Keeping it to that side of the pond, English YouTuber (vlogger, yes, style vlogger), Jim Chapman has must have contemporary classic menswear playbook memorized. Everytime I see a shot of Chapman, I’m immediately impressed by the flattering combinations he puts together that look accessible yet unexpected.



Chance The Rapper

Chance moves on to the next round, cool? Cool.

Prince Harry

Not having custom-designed overalls or his own line of caps or a record label-less Grammy-filled trophy case may put Prince Harry at a disadvantage here. Okay okay, saying a prince is at a disadvantage might be leaning into my bracket bias. While it’s likely his wardrobe is in fact custom from top-to-bottom, we love that Harry’s personal style reads so accessible with easy combos like chinos and button downs or traditional formalwear.




Donald Glover

From a velvet suit at the Golden Globes to skipping a tie under a double-breasted suit, Donald Glover’s red carpet game is airtight. Donald Glover (ahem, Childish Gambino) is a creative powerhouse in his career and it’s safe to say he’s weaving that into his personal style just the same.

Damien Chazelle

Speaking of creative powerhouses who look great in suits (especially when they’re accepting prestigious awards)…Damian Chezelle is relatively new to the red carpet scene, but you wouldn’t be able to tell that from his clothing. He goes for classics, then adds a twist like a bolder hue or interesting pattern.



Justin Timberlake

This SG Madness and “best dressed” mainstay isn’t going anywhere anytime soon. Justin Timberlake continues to evolve his all-American southern style into a dapper force to be reckoned with. While he sticks to staples on the red carpet, we’re all about his dressed down style swerves like bold blazers and bright prints.

Justin Verlander

Did I have to give Verlander a Goog prior to seeding this bracket? Yes, yes I did. Does dating a supermodel improve his style? Maybe. Either way, you can’t help but to praise the way Verlander dresses his athletic frame with confidence and casual-meets-polished pieces.



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