Since his breakthrough role in 2001's Donnie Darko, Jake Gyllenhaal has proven himself one of the most enigmatic leading men in recent history. Whether he's playing a gay cowboy in Ang Lee's groundbreaking Brokeback Mountain, a champion boxer in Southpaw, a creepy photojournalist in Nightcrawler or the baddie, Mysterio, in Spiderman, Gyllenhaal always understands the assignment.
It stands to reason that the Academy Award nominee is one of the most in-demand men on the planet, with a massive eleven films and TV series currently in production, while his Netflix drama The Guilty was released this weekend. In addition, Gyllenhaal has just landed himself the face of Prada's Luna Rossa fragrance.
It's hardly surprising. A red-carpet veteran, Gyllenhaal has long stood as one of the film industry's favourite clothes horses. Case in point: his attendance at the Tony Awards in a blush-pink Prada suit last night and his ultra-sharp, all-white, boxy Valentino ensemble at the Venice International Film Festival for the world premiere of his sister Maggie’s film The Lost Daughter earlier this month.
GQ sat down with Gyllenhaal (via Zoom from New York) to find out what style means to him, who inspires his wardrobe choices and why fragrance is something he can't be without.
Style is self-expression; it's a representation of your mind. Choosing an idea; choosing a mindset with which you align. Wearing an artist or designer's work on your body is an expression of your taste and a choice. Style is about the balance between allowing yourself to come through and expressing an idea that you want to reach out to and become.
My style has changed. I'm trying to move towards understanding that with age there comes a different representation of self, you know, and my clothing reflects that.
People have been telling me what to wear for a long time. I've had a career where there have been a lot of people putting me in things and, if I'm honest, what you've seen me in hasn't always come from my own mind. I am more trained now to dress myself.
Clothing is about the feeling as much as the look. I like to feel good, as well as look good. In turn, that plays into the idea that I look back at things and think, “I felt good then, so it's OK.”
I've worn some things I look back on and regret. There are often looks that feel a certain way in a moment that later on make you just go, “Wow, that was an error.”
There's this brown leather jacket I wore to everything in my twenties. It was tailored at the waist, long and knee-skimming, and it was not good. I thought it was good, but no, looking back, it is a big no. I loved it at the time, but I regret it.
I don't think I take big enough risks when it comes to clothing. I want to look back on my outfits and regret more. I think regretting things you've worn in the past is a big part of self-expression, which to me is vital in being human. That leads to you being better today, whether personality-wise or with your clothes.
I admire my sister's style. I've always been a fan of fashion, but I have always stayed in the same place. Maggie's a lot more adventurous than I am and she looks great for it.
The tailoring of a suit excites me. I get a lot of enjoyment out of wearing one, but also knowing that there's the process of tailoring behind a suit is amazing. I think it's a work of art.
I like a really nice T-shirt. I've tried to convince myself that I can wear a button-up shirt in different ways and that I should be doing that, but if I'm totally honest, a plain T-shirt is what makes me feel and look best.
I really like Morf Vandewalt's style. I played him in Velvet Buzzsaw. He is a risk taker and I admire that. Out of all the characters I've ever done, he's the one with the wardrobe I'd want to raid.
I think with male actors there's this widespread cultivation of a certain idea. Style for male actors is based on the movie stars of the past, which is amazing and they dressed so well, but I think it's exciting to challenge that.
With my style, I consider myself to be pretty old-school to be honest. I like to see people addressing old-school norms and going against them. Jeremy O'Harris is doing that so well, as is Harry Styles. They're just taking risks and flipping what you'd expect people to wear. It's great.
I really like the style of older folks, in British culture in particular; those who have this element of easy elegance and look excellent. Europeans have that more than in the States. I want to achieve that as I get older. With age, there's a different representation of self. Having lived in the UK for several years during my career, I want to be a chilled-out, 90-year-old man in a button-down suit, sipping on an espresso at Ascot.
I like things that have a sentimental value to them. There was a necklace that I wore that for a long time. I wear a number of mixes, but one of them had a little Dumbo pendant, because my mother gave it to me when I was very, very little.
Fragrance is everything to me. I can't be without it. In the same way items of clothing and jewellery can, it immediately connects me to experiences that I've had, whether joyful or terrible. I'm also nose-forward, you know, so I get a sense of personality. I get a sense of what someone's like. I especially think you know what type of person someone is if they spray loads of scent on.
Best-dressed men of the week, from Anwar Hadid to Alex Pettyfer
David Gandy’s Wellwear: ‘We’ve designed the only T-shirt you’ll ever need’
