Round 1 of 2017 Men's Style Madness: 6 VS 11 and 3 VS 14

Bloggers, Ballers, and Beyond

By Gabi Meyers | Last Updated: May 6 2020

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?

6 VS 11

Benedict Cumberbatch

1 | 2 | 3

It doesn’t take a detective to recognize Sherlock’s style. Cumberbatch has a British sensibility, typically opting for more classic cuts in dark neutrals. He can go full-fledged formal in a velvet jacket and waistcoat, but his rainy day ensemble is just as pleasing to the eye.

Eric Decker 

1 | 2 | 3

The New York Jets wide receiver also happens to be a brand ambassador for Buffalo David Bitton jeans. Decker is vocal about his wife’s influence on his wardrobe, crediting her for helping him explore styles outside his comfort zone. We have to say he takes direction pretty well, and her advice certainly looks great on him.

Joe Biden

1 | 2 | 3

As a politician, you can expect classic, simple suits in dark blues, grays and blacks from Biden. The Former VP adds a dose of color with his ties, and you can bet it’s in the shades of red, white, and blue. Biden’s smile is probably his greatest accessory, but his silver white hair is also very on trend. 

Todd Snyder

1 | 2 | 3

You probably know the name Todd Snyder from the label on your favorite pair of pants, but did you know he’s a human with excellent personal style even beyond his clothing brand? His label pushes the envelope in a manageable way (you know I’m in support of his slim cargo pants). He’s the type of designer to adopt a signature look, and his blazer and dark denim combo is a classic that will always feel fresh.

I Am Galla

1 | 2 | 3

A stylish guy that’s willing to divulge his style secrets? Yes, tell me more! Adam Gallagher, the man behind menswear blog I Am Galla, has a wardrobe that is well curated but totally attainable, and he does all the work for you. A guy that’s not afraid to help other guys look their best is an SG Madness winner in my book. 

The Weeknd

1 | 2 | 3

The Weeknd’s style is as on trend as his tunes. His favored silhouette is an oversized jacket, long tee, and skinny jeans, and there’s a whole GQ article about it. He is definitely a strong example of having a signature look and absolutely owning it. 

Idris Elba

1 | 2 | 3

 Idris Elba is a stylish man. He demonstrates the importance of fit, the benefits of going bold with color, and how breaking the (style) rules can sometimes make an outfit that much better.

Bruce Springsteen

1 | 2 | 3

It’s hard not to fall in love with this Jersey boy…I mean, fall in love with his style. He has classic Americana down to a tee, and yes, that was a fashion pun and you love it. Just like you love The Boss. He rocks a spiky faux hawk better than most men half his age.

3 VS 14

Rami Malek

1 | 2 | 3

Rami Malek’s style is interesting, but in a way that easily achievable for the average guy. I have to give a special shout out to the Mr. Robot actor on how well he does fun suiting – both color and pattern. Also, that camp collar shirt and #sockgame in the middle picture is the spring inspo pic I want you boys to be referencing when warm weather finally arrives. 

Leo Chan

1 | 2 | 3

How can we even talk men’s style if we aren’t talking about the man behind menswear site, Levitate Style? Working in the industry helps Chan push conventional style boundaries, which definitely gives him an edge on the competition. His precisely styled coif perfectly complements his classic prep style. 

Oscar Isaac

1 | 2 | 3

More often than not, you can find Oscar in a dark, sophisticated color palette of earth tones and neutrals. He chooses classic cuts and styles that demonstrate what makes classics become classics.

Barry Jenkins

1 | 2 | 3

It’s clear that the director of Moonlight has great style, just take a look at his cool glasses. Jenkin’s style is pretty classic with a few fun colors and patterns here and there, but the perfectly clean tailoring is what really kicks things up notch. 

Riz Ahmed

1 | 2 | 3

This guy has been all over the place this year and I have yet to not like a role he’s played OR an outfit he’s worn. Riz isn’t afraid to flash some style, but he never does so in a way that’s not translatable to the normal guy’s wardrobe.

Brian Boye

1 | 2 | 3

It only makes sense that Men’s Health Fashion and Grooming Editor has great style himself. Brian Boye definitely has fun with fashion, between large scale prints or testing the limits with joggers and cargo pants. As a grooming editor we’re sure Boye knows the importance of hydration, as demonstrated by his wonderful skin. 

Von Miller

1 | 2 | 3

Denver Broncos’ player Von Miller knows the importance of finding frames that fit your face and his style is in your face. He excels at suiting separates, especially when it comes to injecting pattern and color into suit jackets and pants. 

Sam Hunt

1 | 2 | 3

Music, sports, and style star? We think yes. Sam Hunt may be known primarily and secondarily for his college football career and musician status, but he also brings it on in his wardrobe. Hunt keeps things casual most of the time, but when it does come time to don a suit he doesn’t disappoint. 

In partnership with Mirum Shopper for Unilever at Target. Thanks for supporting the brands that make Style Girlfriend possible.