Round 1 of 2016 Men's Style Madness: 7 VS 10 and 2 VS 15

Wrapping up the first round of #SGMadness

Voting is simple: No logging in, and all match-ups are below. Just give it a quick scroll to vote for this year’s Most Stylish Man.

Men’s Style Madness: Round One, 7 vs. 10

Tyler Oakley vs. Idris Elba

Tyler Oakley

1 | 2 | 3

This podcast and YouTube personality has a style that matches his on-air energy and unique perspective. We love that Tyler experiments with color and unique hairstyles, while sticking to classic silhouettes.

Idris Elba

1 | 2 | 3

Back again from last year’s close race (he could’ve gone all the way, guys), this guy keeps this sleek while simultaneously incorporating bold colors and unique details. Between his footwear wins and outerwear style, we can’t get enough of his dapper look.

…Tyler or Idris?

Bradley Cooper vs. Von Miller

Bradley Cooper

1 | 2 | 3

Would it be another year of Men’s Style Madness without an appearance from B.Cooper himself? Probably…BUT Bradley took a few style risks recently that we were big fans of this year. He sticks to his rugged-Americana vibe, and adds interesting textures in surprising ways.

Von Miller

1 | 2 | 3

Even taking his record number of sacks out of the equation, we couldn’t throw enough compliments Von’s way this year. His sneaker game impresses even the most experienced sneaker head, and we love to marvel at his constantly evolving personal style.

…Brad or Von?

Macklemore vs. John Stamos


1 | 2 | 3

We know we know, Macklemore tends to be a tad polarizing. What we can all agree on, though, is his out-of-the-box wardrobe that can throw to multiple retro styles in any one outfit.

John Stamos

1 | 2 | 3

Stamos is just a classic. He’s been on our screens for years and with his Fuller return to the spotlight this year, the unofficial spokesman for a triple unbuttoned dress shirt has updated his suiting with slimmer cuts and stylish shoes.

…Macklemore or Stamos?

Miguel vs. Henrik Lundqvist


1 | 2 | 3

Miguel’s silky smooth singing translates into his 90’s skater-meets-rock god style that he wears on red carpets and on the streets just the same. He doesn’t shy away from man jewelry and we have to commend his his love of unique fabrics.

Henrik Lundqvist

1 | 2 | 3

This Swedish hockey star clearly spends some quality time with his tailor – and it pays off. As a guy normally confined to a uniform, Lunqvist takes every opportunity to show off his personal style with European cuts and impactful patterns.

…Miguel or Henrik?

Men’s Style Madness: Round One, 2 vs. 15

Jimmy Fallon vs. Michael Strahan

Jimmy Fallon

1 | 2 | 3

Our favorite photos of Fallon are the candid shots of his commute from Gramercy to (what we assume) his studio office. Always with a briefcase in hand, he takes a business casual approach to style that is stylish in the most accessible way.

Michael Strahan

1 | 2 | 3

Where hasn’t Michael Strahan popped up this year? We love that he takes risks on red carpets and during his hosting gigs, making for a year-round case study in interesting suiting.

…Fallon or Strahan?

Zayn Malik vs. Jesse Palmer

Zayn Malik

1 | 2 | 3

R.I.P 1D. This “Pillowtalk” pop star was the first to branch off from One Direction and was quick to make his personal sound (and style) mark. His tendency to dress down trousers and mastery of the invisible tie are two strong cases praising his newfound style.

Jesse Palmer

1 | 2 | 3

A big takeaway from our recent Undressed episode with NFL’s Adam Rank: on-air sports guys generally aren’t synonymous with good style. Luckily, that’s starting to change. (Ignoring his hand-in-pocket posing) Jesse Palmer does a great job when it comes to updating his suiting for his body type without going the tapered and slim route.

…Zayn or Jesse?

John Legend vs. Jason Sudeikis

John Legend

1 | 2 | 3

John Legend topped nearly every ‘best dressed’ list possible this year. We saw him shine at the Grammys in a Gucci jacket and we swooned at the sight of his tux at the Oscars – he keeps to classic cuts, thought we love when he branches out with color or pattern.

Jason Sudeikis

1 | 2 | 3

You guys already know our support of all things Jason Sudeikis. This former SNL MVP and decided sneaker head makes the most of adult sneaker style. He sticks to classics like Jordans or minimal low-tops, which looks even more impressive when he perfectly styles them with a suit.

…John or Jason?

Kanye West vs. Taron Egerton

Kanye West

1 | 2 | 3

We have a sneaking suspicion that Kanye loves Kanye’s style – and we have to agree with him. This year he was the talk of the fashion town with his new minimalist line, though we prefer his street style that mixes unique proportions with statement pieces.

Taron Egerton

1 | 2 | 3

Oh Taron, may you never find yourself on the other end of a social media showdown with Yeezus. Ever since his standout performance in Kingsman: The Secret Service (really though, when is the sequel happening?), we’ve loved seeing his style transitions between staple sneakers and traditionally preppy looks.

…Yeezy or Taron?


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