Annual best-dressed lists often make little sense. That's because a whole lot of backroom politicking and planning go into them. So Esquire is once again asking you, dear reader, to decide upon our Best-Dressed Man of the Year. Last week, Sebastian Stan fought his way into the semi-finals. And so it's onto a battle of great magnitude: Tom Hiddleston vs. Harry Styles.


Note: voting is now closed

After weeks of voting and deciding (thanks for that), we're finally onto the semi-finals. And it's quite the showdown: two titans of their respective industries, and two men that lots of women (and men) love with wild abandon. It's Harry Styles and Tom Hiddleston.

For the latter, a standout year. It's set to continue, too. There are talks of a new season of The Night Manager. There are talks of a Loki standalone on Disney+. And all that, likely, means a continuation of press event outfits that always work: rock solid navy suits, with varying degrees of experimentalism. Oh, and they're usually by Ralph Lauren's Purple Label.

tom hiddleston harry styles
Patricia Schlein/Star Max

Though not the weird kind of experimentalism. The 38-year-old is a classicist through and through. He follows the rules. And in his case, nice guys finish first. Or in the semi-finals at the very least.

All of which is a huge contrast with Harry Styles. After avoiding the spotlight in between album launches, the former Directioner is back on the campaign trail. Rejoice, for that's meant a slew of looks that are, actually, incredibly experimental.

tom hiddleston harry styles
James Devaney

So much so that we saw flares, and dangly pearl earrings, and Bovidae-emblazoned sweater vests and lots of things that shouldn't really work. And yet here we are, bearing witness to a boybander-turned-pop-deity who has not only been released from Simon Cowell's production line, but has shed that identity almost entirely.

So, who wins? The man who dips his toe in the unusual, or the man swimming in the deep end?

harry styles tom hiddleston
Ana Davila