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, Henry Golding edged out MBJ for the win. So it's onto round four: Timothée Chalamet vs. Benedict Cumberbatch.


Note: voting is now closed.

For years, actors kept the showmanship on-screen. Their craft is to depict characters, and it's a serious craft, so it made sense, then, to keep things serious off-screen too. That often meant classic stuff: the two-pieces, the crisp shirts, the holy trinity of grey, black and navy.

But the ground is shifting. As men lean into the big menswear without worry or judgement, they've been pushed there, arguably, by the big names who do the same. On one side, you've Timothée Chalamet: the rising star that took big risks from the off. On the other, Benedict Cumberbatch, the quintessential British thesp that was more gradual in his steps towards the left-field. And both are head-to-head for round four.

For the latter, it was a fool-proof formula. Handsome face, plus actual talent, multiplied by critically-lauded gigs equals one very hysterical internet. If that wasn't enough to win over the Twitterverse though, Chalamet punctuated the ascendant fame with looks that were just as notable as any occupational medieval bowl cut.

timothee chalamet benedict cumberbatch
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2019 was no different. We've had a painter-decorator from the year 2073. Then, electric yellow under a suit. A nod to queer culture in a Louis Vuitton harness. Glittery hoodies. Intergalactic space tailoring from Haider Ackermann. And, just this morning, Chalamet was pictured in a bolt of head-to-toe cobalt blue at The King's premiere. The risks are endless, and for the 23-year-old, they've paid off.

It wasn't deep end diving for Cumberbatch, though. On the back of a successful year, the Shakespearean trained actor began with the sensible stuff: razor-sharp suits, blues for Wimbledon, that sort of thing.

The first premonition of a change came when the Avengers star stepped out in New York, resplendent in the burnt orange streetwear that leaves your female friends' WhatsApp messages blue ticked. It was current, and cool, and not at all what we were expecting.

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Getty Images

And then the Met Gala happened. Cumberbatch broke the internet by doing the unsuspected: an all-white Cuban land baron at a 24-hour Miami disco. Of course, this was fancy dress - the Gala's abstract theme was derived from Susan Sontag's seminal essay, Notes On Camp. But in a sea of half-hearted attempts to fully understand Sontag's complex theorem, Benedict was a beacon of Liberace splendour.

So, who wins? The actor that never left the left-field, or the star that's slowly moved in?

timothee chalamet benedict cumberbatch
Ana Davila

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