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 turns 40 on December 19, been nominated for an Oscar and starred in a string of hit movies, he’s become known for his style both on and off screen.

In honour of his birthday, here we look back at some of the Hollywood heartthrob’s best fashion moments…

Actor Jake Gyllenhaal arrives for the UK premiere of “21 Grams” – as part of the Times BFI London Film Festival – at Odeon West End in central London. (PA Archive)

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.

Actor Jake Gyllenhaal during his guest appearance on MTV TRL UK at the MTV Studios’s in Camden. (PA Archive)

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.

Actors Jake and Maggie Gyllenhaal. (PA Archive)

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

Brokeback Mountain premiere

Jake Gyllenhaal arrives at the premiere of his new film Brokeback Mountain. (PA Archive)

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

Decked out in double denim, shearling lined coats and stetson hats, Gyllenhaal’s wardrobe in Brokeback Mountain, for which he received an Oscar nomination in 2006 for best supporting actor, was all about cowboy cool.

Jake Gyllenhaal, nominated in the Best Performance by an Actor in a Supporting Role category for his part in Brokeback Mountain arrives on the red carpet. (PA Archive)

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.

AP OUT: Jake Gyllenhaal attends a photocall for his new film Zodiac at the Palais Des Festivals, during the 60th annual Cannes Film Festival, Cannes, France. (PA Archive)

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

AP OUT: Jake Gyllenhaal arrives at the premiere for new film Rendition, part of the Toronto Film Festival, at the Roy Thomson Hall in Toronto, Canada. Picture date: September 7th, 2007. (PA Archive)

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.

Life Photocall – London (PA Archive)

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

Jake Gyllenhaal attending the Spider-Man: Far From Home Photocall held at the Tower of London. (PA Archive)

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 during the filming for the Graham Norton Show at BBC Studioworks 6 Television Centre, Wood Lane, London, to be aired on BBC One on Friday evening. (PA Archive)

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.

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