Jake Gyllenhaal is really on top of the acting game. The reason: he's hit pretty much every genre on screen, from his early days playing a cynical teen in Donnie Darko and gay cowboy in Brokeback Mountain to his more recent repertoire that includes playing a champion boxer in Southpaw and creepy photojournalist in Nightcrawler. His biggest role as of late? Mr Mysterio in Spider-Man: Far From Home.
That's a pretty impressive range and his current style game follows the exact same pattern. Over the past year alone, Gyllenhaal has dipped into every section of his wardrobe, from statement printed suits and timeless essentials to winning accessories. There's a lot to learn from this fashion sense, so we thought it was about time to celebrate his best recent style moments. Wardrobe upgrade imminent…
When: 17 October 2019
Why it works: Gyllenhaal is proving the power of a slim-cut, single-breasted black suit here, while also giving a successful nod to autumn through his base layer. 'Tis the season to sport a turtleneck and Gyllenhaal's one of choice is clad in a warm, burnt orange hue. It makes for a classic colour combination, as well as a subtle nod to the Seventies (which we're definitely fans of).
When: 21 June 2019
Why it works: Scared of styling white jeans? Jake Gyllenhaal has a tip for you: style a white jean jacket instead. It works with pretty much anything, but he chose to wear it with a black T-shirt, some slim-cut grey trousers and Oxford boots. Layer a light brown overcoat on top of the jacket to survive this temperature-dropping season.
When: 9 June 2019
Why it works: Bored of your old and trustworthy black suit? Gyllenhaal advises you branch out to a chocolate brown tailoring palette instead. Arriving to the Tony Awards in this three-piece set from Ermenegildo Zegna, the elegance was in the details: shawl lapels, a Mandarin collar to his shirt and lace-up brogues. Very nice.
When: 14 February 2019
Why it works: Print isn't easy to pull off, but if you opt for a simple one in the right shades (shoutout to Dries Van Noten's wave print of the year) you'll be making a solid case for it. Good job by Gyllenhaal, then, who embraced Noten's range of romantic pink shades through his tailoring and kept the styling super minimal (we do love a trustworthy white T-shirt).
When: 8 August 2019
Why it works: Ah, the double-breasted suit. Jake chose to base his tailoring with a T-shirt once again, allowing the suit's formal details to really stand out. In this instance, he's raking up points through those sharp peak lapels, eye-catching black buttons and the slate grey shade in itself. He's sourced the suit from The Row's menswear line, so stripped-back chicness was pretty much guaranteed here.
When: 26 June 2019
Why it works: How to master the transitional suit from day to night? Like Jake Gyllenhaal. Navy is a good point of call for any event and looks especially good with a forest green shade. Some details on Gyllenhaal's attire then: the single-breasted structure to his suit is slightly less formal, partnered with a casual jumper, simple gold chain and patent slippers. Formal insouciance, achieved. We'll be emulating this as soon as possible – cheers, Gyllenhaal.
When: 26 September 2021
Why it works: Gyllenhaal attended the 74th Annual Tony Awards in New York City. Sure all eyes were on the stage, but we couldn't help but faun over the actor's baby pink tuxedo. Not for the faint-hearted, the Prada creation has an ever so slightly oversized fit, which suits Gyllenhaal's nonchalant style.
When: 29 September 2021
Why it works: For the premiere of "The Lost Daughter" (that's his sister Maggie's movie) during the 59th New York Film Festival, Gyllenhaal heralded the end of summer and the beginning of autumn with a deep teal velvet two-piece.
When: 6 November 2021
Why it works: Dressed in Gucci, Jake Gyllenhaal was a snack in the delicious colours of Nestlé's retro Butterfingers at the 2021 LACMA Art+Film Gala.
Now read:
Jake Gyllenhaal: his best movies on Netflix
Jake Gyllenhaal on Tom Holland: 'I really, truly do love the kid'
