Round 1 of 2018 Men’s Style Madness: 6 VS 11 and 3 VS 14

Round 1 of 2018 Men’s Style Madness: 6 VS 11 and 3 VS 14

Week 1's almost done

By Megan Collins | Last Updated: Jun 23 2022 | 5 min read

We’re almost through Round 1 of SG Madness. Cast your votes for our 6-seed versus 11-seed matchups, and 3-seed versus 14-seeds, below.

6 VS 11


Trevor Noah

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1 | 2 | 3

When it comes to looking good in his clothes, does it help that The Daily Show host was blessed with the height and lanky frame of a runway model? Sure, but he still knows how to put outfits together in an interesting way, and always goes the extra mile to make sure his looks stand out and feel like a l’il something special. Nothing funny about that.

Armie Hammer

1 | 2 | 3

Team SG’s Taylor Davies picked Hammer to go all the way. So we’ll let her make her pitch:

“Listen – everyone loves Trevor Noah, and I’m not trying to take away from him…as a person. But the plain fact is that Armie was cruising around Europe and beyond in a gorgeous array of track suits while promoting Call Me By Your Name, and it was a “thing” and I loved it.

Also, his burgundy velvet tux at the Oscars looked better than a big glass of red wine on a cozy winter’s evening. He looks like a Ken doll come to life, I know, but boy can that man dress.”

Noah v. Hammer

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Lewis Hamilton

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1 | 2 | 3

Do we follow Formula One racing? Not a chance. But Hamilton’s made a name for himself off the track (track? is that even what you call it?!) with his edgy, on-trend looks, helping us notice him without his helmet on. 

Timothée Chalamet

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1 | 2 | 3

Timothée Chalamet came out of the style gate strong this year during the press tours for both Lady Bird and Call Me By Your Name, and during the subsequent awards season dog and pony show. Even if we don’t love all his choices, we have to respect how much thought he puts into his wardrobe at 22, which we definitely didn’t at that age. Hell, we still don’t most of the time, and we do this for a living. 

He’s also Taylor’s runner-up favorite, so we’re interested to see how far you think Timmy should go. 

Hamilton v. Chalamet

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Russell Westbrook

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1 | 2 | 3

OKC’s Russell Westbrook boasts a personal style that’s way better than just OK (see what we did there?).

Is all of it wearable for the “average” guy? Nah, but when an NBA locker room waits at the end of your runway, you’re bound to take some fashion chances.

Darren Criss

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1 | 2 | 3

Remember Darren Criss? From Glee? He’s back, and he’s playing a murderer on that Versace American Crime Story and showing up places to promote it looking like..well, looking like he does above. Namely: fresh and snazzy. These days, the only thing he’s murdering is the fashion game.

Westbrook v. Criss

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Joe Keery

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1 | 2 | 3

Okay, sure, name recognition for Joe Keery may still be relatively low (Megan kept calling him “Steve from Stranger Things” until the intern finally subbed his actual name in on the bracket), but everyone can agree he’s a style standout among the cast.

Sure, that hair does a lot of the heavy lifting, but details like cuffed pants, retro button-ups, and bare ankles take him the rest of the way towards well-deserved style star status.

Milo Ventimiglia

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1 | 2 | 3

As Jack Pearson, the patriarch of NBC sobfest This Is Us, Milo Ventimiglia makes early ’90s business casual look…well, totally sexy. Off the set, the actor’s throwback motorcycle tough guy with a heart of gold vibe makes us feel very safe in a way that a slow cooker never will again.

Keery v. Ventimiglia

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3 VS 14


Chris Paul

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1 | 2 | 3

That bomber! That blue suit with sneaks! The hoodie under the houndstooth! Did we mention the bomber?? Chris Paul can do no wrong in our eyes; how about yours?

Jonah Hill

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1 | 2 | 3

Jonah Hill looks like a lot of NYC and LA (or NYC-LA hybrid) guys we know…trendy but not in your face about it. Kind of a hypebeast, but in a low-key way that makes us not want to blow our brains out over brunch listening to them talk about the latest Supreme drop.

Plus anyone who can pull off denim-on-denim in such close shades (and he does!) deserves a hat tip.

Paul v. Hill

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Dwyane Wade

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1 | 2 | 3

If we had to imagine how a bazillionaire basketball player living in Miami with a famous and gorgeous actress wife would dress, we’d dream up Dwayne Wade’s wardrobe, head to toe. Bottom line? If this man is wearing it, we’re probably gonna like it.  

Sam Rockwell

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1 | 2 | 3

We hit up Rockwell’s stylist Michael Fisher for insight into the newly-minted Oscar winner’s stellar looks during awards season.

Fisher says, “I built the wardrobe around his ‘Tony ManeroSaturday Night Fever’ vibe. Sam has some slick moves and we wanted his suiting to reflect that. His adventurous spirit and sense of humor led easily to the most-talked about men’s styling moment of the season.”

Indeed, GQ declared ‘Sam Rockwell makes Danger Zone style look pretty good‘ and we’re inclined to agree.

Wade v. Rockwell

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Harry Styles

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1 | 2 | 3

This year, Harry Styles had a full-on Fashion Moment™ and it seems the whole #menswear world was on board. If you’re into uber-fashion-y suits, and a decidedly throwback vibe, you’ll be into the former One Directioner’s solo act style.

If not, well, that’s okay. Not everyone can pull off a brown bell bottom suit with dragon embroidery. And we’re fine with that.

Adam Scott

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1 | 2 | 3

Tiger may be back, but it’s golfer Adam Scott’s style that really has us excited. Fresh off a partnership with Uniqlo, the Australian pro brings a fresh fashion sensibility to the green.

Styles v. Scott

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Odell Beckham Jr.

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1 | 2 | 3

NESN’s Courtney Cox says, “OBJ’s style keeps us on our toes! He know’s how to make a statement when he dresses down with lots of layers while ALSO dressing (to impress) up. He mixes patterns and looks SO cool while also looking very polished.  OBJ is a legend both on and off the field.”

Kit Harington

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1 | 2 | 3

GoT’s Jon Snow shows us just how important tailoring can be for smaller guys. At 5’8,” the heir to the Iron Throne always rocks just the right break (ie, none at all) and a slim fit that’s, well…fit for a king.


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