Round 2 of 2016 Men's Style Madness: 1st heat

Who's ready to talk upsets?

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.

Nick Wooster vs. Ryan Gosling

Nick Wooster

1 | 2 | 3

Talk about upsets *listens to Gabi cheer in the distance*…Wooster beat Biebs by a landslide in Round One and we can’t say we’re too shocked. This #menswear pro loves a minimal sneaker and blends casual pieces with unconventionally cut suiting staples in cohesive looks that are always camera-worthy.

See more ways to wear minimal sneakers.

Ryan Gosling

1 | 2 | 3

Our MVP of rugged style (that some people are hedging their bets on this year) is a prime example of making a simple style your own with interesting details like unique outerwear or even some man jewelry.

…Wooster or Gosling?

Oscar Isaac vs. Rami Malek

Oscar Isaac

1 | 2 | 3

So long, Drizzy. In a slightly less surprising upset, Isaac – and his elegant style – took the lead against Drake in the first round. It’s impressive that you guys are rewarding overall classic style versus more trendy vibes, and we have a feeling this round is going to have so close match-ups.

Rami Malek

1 | 23

…Speaking of close match-ups. Rami Malek takes a similar approach to everyday style – he always looks put together, but doesn’t shy away from interesting color combinations or nods to street wear style.

Another way to wear monochrome. 

…Oscar or Rami?

Barack Obama vs. Leon Bridges

Barack Obama

1 | 2 | 3

The Obama vs. Pinault match-up was an incredibly close one, but it looks like you guys favor his suited staples and khaki adjacent off-duty wardrobe. His gala and formal style has consistently become more dapper, so we’re intrigued to see how this next round will play out.

Leon Bridges

1 | 2 | 3

Ow ow (can you hear Brit chanting his name?), it was a blowout  between Leon Bridges and the Chris Martin in the first round. Bridges’ retro style is a refreshing wink at the power of past sartorial days, but we love how he infuses that with today’s cuts.

How to incorporate retro style at the office.

…Obama or Bridges?

Eddie Redmayne vs. Cam Newton

Eddie Redmayne

12 | 3

Redmayne can definitely back up his high bracket seeding on the red carpet or simply walking the streets. His strengths in color and pattern are only made that much better by the precise tailoring we see in every outfit he wears.

Cam Newton

1 | 2 | 3

Another powerhouse in color and pattern, Super Cam never hesitates to reach for an unexpected piece that’s sure to standout. What’s really impressive, though, is how he takes those bold pieces and molds them into classic cuts and styles the rest of his look in a way that isn’t overwhelming.

…Eddie or Cam?


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