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, Cumberbatch bested Chalamet. So it's onto round five: a wildcard in Barack Obama, vs. Jake Gyllenhaal.
Note: voting is now closed.
Actors and politicians aren't so different. They aspire to win hearts and minds. They're gifted in the art of persuasion (or at least they should be). And both are obsessed with 'the optics': good optics being an Academy Award nomination, or having working-class people laugh with you; bad optics being a Hollywood breakdown, or having working-class people laugh at you.
Optics also extend to the act of looking good, and once again, two leaders in their respective fields are united: Barack Obama and Jake Gyllenhaal. They dress well. They break the mould doing it. They just do so in their own very unique way.
For the former occupant of the White House, great style means dressing down the stringent codes that were required behind the Resolute desk. There are fewer ties, for a start, and more comfortable-looking suits. More Iowa steak fry, less State of the Union. What's more, it's a lead on from the big meme tracksuit, when the former POTUS was pictured in a black tracksuit just days after leaving office. Obama is relaxing. He wants you to know it.
And, in an age when viral presidential moments are often of the inflammatory, syntactically confusing sort, Barry did the opposite: a Rag & Bone bomber jacket above all-black at a basketball game. But the best part? The number '44' stitched to the sleeve (that's Obama's number as the 44th President of the United States, by the way).
It's wild for a politician, but wouldn't make much of a stir out west. Jake Gyllenhaal, after filling the role of nice boy next door who drops your sister off on the dot, is having something of a style renaissance. Silhouettes have relaxed. Colour is worn with reckless abandon. He even aired a psychedelic seventies sofa print in a sharp two-piece from Dries Van Noten.
All of which points to Gyllenhaal's new role as a risk-taker at large. Most actors settle for the classic stuff (the logic being that statements are to be made on-screen, not the red carpet), the 38-year-old is bucking the trend and going big. Really big, actually.
So, who wins? The president on a much-needed lieu day, or the actor that's refusing to take a day off? Vote now.
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