Annual best-dressed lists often make little sense. That's because a whole lot of backroom politics and planning go into them. So this year, Esquire is asking you to decide the Most Stylish Man Of The Year in a tournament for the ages... Last week, Tom Hardy sailed to victory over Daniel Craig, and it's onto the penultimate round of the knockouts.

The seventh round of our attempt to find the Most Stylish Man of 2018 is a case of Hollywood heavyweight vs breakout star as Leonardo DiCaprio takes on Chadwick Boseman.

Getty Images, Rex

As a man we've all wanted to be at some point over the last 27 years, DiCaprio has no time for trends in 2018 (unless you count vaping). For a rare step-and-repeat appearance at the Good Money Gala, the Once Upon A Time In Hollywood star went for something wholly classic: a tonal blue two-piece in a razor-sharp fit with all the right accessories, as foolproof a formula as casting him in your movie.

A similar tonal thread has extended to his causal outfits too. While the 44-year-old often goes incognito in signature, celeb-incognito sweats and shades, CinemaCon 2018 saw DiCaprio opt for a memorable suede bomber in a slimline fit that perfectly flattered his six foot frame.

Chadwick Boseman, Marvel's man of the hour and the upcoming 17 Bridges star, has marked his rise by rejecting the Old Ways. He's unafraid of pastels. He's unafraid of prints. And, frankly, he's unafraid of you.

Take his look for the 2018 ESPYS. Wearing Virgil Abloh's reinvented Louis Vuitton, Boseman pulled off the tricky all-over white with the now iconic harness holsters. This is as far from classic as you'll get.

Getty Images

Then, may we refer you to Boseman's Oscars get-up. Once a place of penguin suits a plenty, the actor eschewed standard black tie for something more statement; specifically, a longline gold-gilted dinner jacket above a Mandarin collar.

So, who gets to be the menswear mayor of Hollywood? DiCaprio, our reigning classicist supreme, or Boseman, a man that's writing out his own rulebook? Don't boo: vote.

This content is imported from {embed-name}. You may be able to find the same content in another format, or you may be able to find more information, at their web site.

Ana Davila

This content is created and maintained by a third party, and imported onto this page to help users provide their email addresses. You may be able to find more information about this and similar content at piano.io