Edgar Ramirez vs. Chris Pine

Ramirez took out Mahershala Ali in our Round of 64, MOTY cover man Ryan Reynolds in our round of 32, and now takes on Captain Kirk himself, Chris Pine, in this round. Does the sartorially-adept Girl on the Train actor have what it takes to keep on keepin' on to the Quarterfinals? Or will Pine's knack for wearing everything—from swanky double-breasted suits to short-sleeve patterned shirts—put him in the top spot instead?

Lewis Hamilton vs. Tom Ford

The flashy Formula 1 driver goes up against the king of ultra-luxe menswear. On one hand, you have Lewis, a Balmain and DSquared label-loving fearless dresser. On the other hand you have Ford, a man who almost never leaves the house in anything other than a sharp-as-hell black suit and a swath of exposed chest hair. Who do you want to move on, the swervy sportscar driver or the uniform style master?

David Beckham vs. Tom Hiddleston

Who's your favorite stylish Brit? Is it the former soccer great who's as well-known for what he wears to the airport as he was for what he did on the pitch or the could-be Bond and former Taylor Swift flame, who never met a well-cut suit he couldn't pull off?

Rami Malek vs. Justin Theroux

Here are two men who know how their clothes should fit. Look at any shot from the last twelve months and just try to find a pooling trouser or a bulky jacket in their respective collections of fits. Malek has made the most of his Mr. Robot-fueled ascent to A-list status, turning up to red carpets in an arsenal of Dior Homme suits that continue to impress us. Theroux, meanwhile, is the leather jacket-loving all-black-everything badass who made us want a $400 T-shirt this year. Only one man can move on.

Kanye West vs. Conor McGregor

Well this just got interesting. West breezed by his Donda team member Virgil Abloh in the first round and easily took out Tyler, the Creator in the second. new new Trump's new longtime buddy can be credited with sparking many of 2016's most prevalent menswear trends, from sock-upper sneakers to garment-dyed sweats (plus merch, merch, and more merch). McGregor, meanwhile, is the UFC spitfire who's never-not fearless approach in the ring applies to his wardrobe as well. Which outspoken lightning rod deserves to keep on fighting for this year's top spot?

Roger Federer vs. Steven Yeun

We'll be the first to admit we didn't expect these two underdogs to make it this far. Don't get us wrong, both the tennis great and Walking Dead actor know what they're doing in the style department, it's just any man up against menswear gods like Gosling, as Federer was last round, or Aziz Ansari, as Yeun was in Round 1, would prove hard to overcome. But here we are, with a matchup that pits the understated, elegantly stylish Swiss sportsman against the actor who's mastered everyman dressing (that's a very good thing).

Jared Leto vs. Young Thug

All you need to ask yourself here is: which style maverick made more Internet-burning menswear moves in 2016?

Donald Glover vs. Jaden Smith

So we wound up with two of our favorite guys to spot on the red carpet going against each other to advance to the quarterfinals. Both Glover and Smith have more personal style than just about any other famous guys we know right now and, more importantly, neither dresses like anyone else out there today. So who's steez are you behind, the casually suited Atlanta star or the swerviest teen on planet Earth?

Watch Now: See GQ’s Super Stylish Men of the Year Party Video Portraits