Kanye West vs. Tyler the Creator

Our two-time defending Most Stylish Man champion started 2016 off with a bang, riding in on a wave of still piping hot Yeezy hype and an arena's worth of Life of Pablo merch. The rapper/designer's Yeezy Boosts continue to sell out in seconds and those gothic font Pablo tees are to thank (or blame) for all of the artist merch you see today. Tyler is 2016's other rapper turned designer whose colorful Golf Wang lineup is the perfect distillation of his own personal style. What's your preference: High fashion sweats or subversive sportswear?

Conor McGregor vs. Drake

Here are two men who know the ultimate power of killer outerwear and how to harness it to their advantage. McGregor is the trash-talking, wildly entertaining UFC sensation who doesn't shy away from swanky three-piece suits or pimp-level Gucci furs. Drake, of course, is everyone's favorite rapper with all the feels who turned his love of things cozy into OVO, his label of cool kid sweatsuits and hoodies and never met an flex-level outerwear piece he didn't like (or wear). Only one can continue on in this year's Most Stylish Man battle.

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Ryan Gosling vs. Roger Federer

Our January cover man faces off against the tennis ace who can wear the hell out of a turtleneck. Gosling, of course, is the #menswear icon who never met a swervy well-tailored suit he didn't' like and does things like pull off actual pajamas out in public. And while the La La Land actor is known for his retro-tinged wardrobe, Federer is a man who reminds us why the classics (dove gray suits, v-neck sweaters) are timeless. It's not easy to knockout Gosling but then again, we're not underestimating the power of the #3 ranked player's loyal fan base.

Nick Jonas vs. Steven Yeun

Nick already pulled off the ultimate upset, taking out brother Joe in the first round of this year's showdown. But does he have what it takes to defeat Yeun and his army of The Walking Dead fans still mourning Glenn's death? Hard to say. Yeun has the everyman style thing down pat thanks to wardrobe of quietly stylish staples that never look out of place no matter what event he's attending. Jonas, meanwhile, is happy to run the menswear gamut, turning up in classic tailoring one minute and stage-ready drapey tees and bomber jackets the next.

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Jared Leto vs. Shia LaBeouf

It hurts us to put these two mavericks against each other, but that's what the people wanted. What can we say about either of these men in 2016 that you don't already know. Leto had a breakout year getting more press for becoming the Joker than the movie he played the character in and became Alessandro Michele's favorite living mannequin for all things Gucci. LaBeouf started his ascent back to A-list status on screen and off, decided he was an amateur rapper and finally explained why he dresses like a broke college student. Who's your preferred style outlier?

Young Thug vs. Luka Sabbat

Young Thug a.k.a. Jeffery is a talented rapper with zero interest in what you think of his fits, and even less interest in whether or not his wardrobe comes form the women's section of a store. Sabbat is a founding member of the new Cool teen™ pack, a crew of barely two-decade old kids with signature personal style that folks twice their age can't claim. These are two guys who ooze DGAF-ness when it comes to what they wear and helped make this year in menswear so damn enjoyable. That said, only one guy can advance to the Round of 16...

John Mayer vs. Donald Glover

Both Mayer and Glover know just what they're doing when getting dressed, but neither one makes a big deal out of it. Sure, Mayer has a predilection for rare artisanal kimonos, sea island cotton tees, and boatloads of Visvim, but you wouldn't necessarily pick that up on first glance (you would think "this guy knows how to wear a t-shirt and jeans damn well."). Glover always impresses us with his ability to wear classic suiting the way we wear sweatpants and basic wardrobe essentials look not, well, so basic. It's a head-to-head matchup of understated style and only one man can walk away the victor.

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Jaden Smith vs. Hasan Minhaj

This matchup encapsulates why this showdown is so much fun. On one hand you have the crown prince of Calabasas, the inventor of Cartier rings as hair ties, the only human on the planet who can pull off overalls (kind of). On the other hand, you have the fake newscaster who dresses better than any actual reporters we see on TV. Honestly, these two guys couldn't be on more opposite sides of the the menswear spectrum, so there's no telling which one will come out on top.