Round 2 Men’s Style Madness 2017: 4th heat

Round 2 Men’s Style Madness 2017: 4th heat

The bold and the style brave

By Megan Collins | Last Updated: Apr 22 2019 | 3 min read

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?

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 Dev Patel vs. Tom Hiddleston

Dev Patel


Dev Patel seems like the type of guy who could take you to a museum before swinging by a red carpet premiere within a four-hour span of time. He also seems like the type of guy who would comfortably wear the same outfit for both activities – and that’s a quality we always admire. As for his tasseled quaff? We can only imagine the gold mine of hair product he must be sitting on to achieve that effortless look.

Tom Hiddleston


Speaking of impeccable hairstyles…Nice to see you again, Sir Hiddleston. We’re not surprised to see he’s made his way from Asgard to Skull Island to SG Madness, but we’re sure glad he’s here. Hiddleston’s off-duty style of sweaters and relaxed dress shirts is something any guy can replicate – and we highly encourage that they do.

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Michael Hainey vs. Chance The Rapper

Michael Hainey


Let’s hear it for Hainey and his timeless take on Esquire-meets-#menswear. He’s never afraid to tackle a textured combination with a pop of pattern (and a perfect fit). A quick way to try his style for yourself: Pair two patterns of different sizes together, and add a suede shoe to boot.

Chance The Rapper


C-h-a-n-c-e. Need I go on? Probably not, but with photos like these I’m feeling particularly inspired. We love that he goes head-to-head with classics like a henley or denim jacket and always comes out on top by adding his personal touch to any style.

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J. Balvin vs. Donald Glover

J. Balvin


A bold animal print? You got it. A tailored tracksuit? Oh, yes. Ever-evolving hair makeovers? Claro que si! This Colombian crooner’s energetic style choices highlight his fearless confidence, which is always a refreshing way to go about personal style.

Donald Glover


The direct path straight into our hearts: Subtle suiting risks. Glover’s ability to pull off an unexpected dress shoe or a unique suit combination is praiseworthy and surprisingly easy to try in everyday life. We love that his tailored looks enhance his frame without looking too slim. Also, can we shout out his facial hair or what?

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Damian Lewis vs. Justin Timberlake

Damian Lewis


Red carpet scarves, slightly popped blazer collars, dress shirts with jeans. This Billions star has definitely found a personal style that makes him feel like a million bucks. You heard it here first: Lewis’ “never let ’em see you sweat” vibe coupled with his slim fit tailoring is a look worth stealing.

Justin Timberlake


The definition of forever calm, cool, and collected (on or off the red carpet). Sure, J.T. is a Hollywood mainstay, but his style remains hometown accessible.

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