As Jake Gyllenhaal Turns 40, We Take a Look Back at His Best Fashion Moments

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Jake gyllenhaal style
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Since shooting to fame with 2001’s Donnie Darko, Jake Gyllenhaal has enjoyed nearly two decades of silver-screen success. Not only has the actor – who turned 40 in December – been nominated for an Oscar, and starred in a string of hit movies, but he’s also become known for his style both on and off-screen.

In honor of his birthday, here we look back at Jake Gyllenhaal’s Style from the Noughties to today.

'21 Grams' Premiere

Usually at movie premieres, it’s all about the tailoring for men, but we love this double-breasted coat and scarf combo at the London premiere of 21 Grams in 2003.

Jake Gyllenhaal Style 21 Grams Premiere
Photo: Courtesy of PA Images

MTV's 'TRL Live'

Remember the Noughties when wearing a T-shirt over a long-sleeved top was the height of cool? This is such a throwback look it’s sure to be back in fashion soon.

Jake Gyllenhaal Style MTV TRL Live
Photo: Courtesy of PA Images

The Vanity Fair Party

Gyllenhaal kept it classic on Oscars night 2005 in black tie while attending the annual Vanity Fair after-party with sister Maggie.

Jake Gyllenhaal Style Vanity Fair Party
Photo: Courtesy of PA Images

'Brokeback Mountain' Premiere

He switched it up for the Venice premiere of critically acclaimed Brokeback Mountain, choosing a chic grey suit with a bright orange tie.

Jake Gyllenhaal Style Brokeback Mountain Premiere
Photo: Courtesy of PA Images
Jake Gyllenhaal Style Brokeback Mountain
GIF: Courtesy of PA Images

Academy Awards 2006

He may have lost out to George Clooney in the best supporting actor category, but Gyllenhaal sure looked dapper on the red carpet at the 2006 Oscars in a timeless black tuxedo.

Jake Gyllenhaal Style Academy Awards 2006
Photo: Courtesy of PA Images

Cannes Film Festival

The following year, Gyllenhaal showed off his summer style credentials in Cannes, donning an understated suit and lavender shirt.

Cannes Film Festival Jake Gyllenhaal Style
Photo: Courtesy of PA Images

'Rendition' Premiere

Making an appearance at the Toronto Film Festival later that year, the actor added a V-neck jumper to the mix with his usual dark suit.

Jake Gyllenhaal Style Rendition Premiere
Photo: Courtesy of PA Images

'Life' Photocall

Opting for a more casual look while promoting the sci-fi movie Life in the UK in 2017, Gyllenhaal teamed dark jeans with a classic black blazer and T-shirt.

Jake Gyllenhaal Style Life Photocall
Photo: Courtesy of PA Images

Spider-Man Photocall

Back in London in 2019 on the promo tour for Spider-Man: Far From Home, in which he plays Mysterio, the actor chose a more fashion-forward look than we’re used to seeing him in, sporting a pale blue collared leather jacket.

Jake Gyllenhaal Style Spiderman Photocall
Photo: Courtesy of PA Images

'The Graham Norton Show'

One noticeable addition to the actor’s wardrobe in recent years has been a simple gold chain, as seen on The Graham Norton Show in 2019. Worn with suits, T-shirts, and knitwear alike, it’s a subtle but stylish touch.

Jake Gyllenhaal Style The Graham Norton Show
Photo: Courtesy of PA Images
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