Jake Gyllenhaal Is the King of Easygoing Shirts

Over the past few months, Jake Gyllenhaal has had his fair share of big style moments. There have been Prada coats, Wooyoungmi suits, and ’90s denim-tailoring fits. But one thing that always bang are his shirts.

Gyllenhaal’s most recent turn is maybe one of the best yet. Spotted in Manhattan at the Tribeca Festival premiere of Presumed Innocent, his latest Apple TV courtroom thriller that’s steered by the same production company as Big Little Lies, the actor went for Sopranos lite: big, boxy, and just bold enough without going into “And in this house, Christopher Columbus is a hero!” territory.

Jake Gyllenhaal and his Presumed Innocent co-star (and brother-in-law) Peter Sarsgaard at the Tribeca Festival.

Dimitrios Kambouris/Getty Images

The shirt is Prada, but let’s start with the collar. Instead of a classic straight turn, it’s Cuban. It’s laidback. It’s self-assured. And, since it’s a collar that suits those with broader chests, it’s the perfect fit for an actor that got absurdly yoked for for his most recent movie, Road House. The flowy silk finish means it will survive the summer heat, too.

Then, there’s the print. The geometric pattern takes its cues from the ’70s. It’s understated. It looks like a shirt he might have copped at Brooklyn Flea rather than Prada. And that makes us all the more into it.

The rest of the fit goes hard, too, from the straight-leg trousers to the white tank and tassel loafers—all of which are also by Prada. It’s nothing showy. Nothing loud. Just good, solid menswear worn by a good, solid actor. On his wrist, Gyllenhaal’s regular watch of choice: a Cartier Santos. (Since he was announced as Cartier’s first-ever watch ambassador in 2018, this comes as no surprise. It’s a timepiece that’s favored by Tom Holland and Tyler, the Creator, too.)

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