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…

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.

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.

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.

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.

Brokeback Mountain

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.

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.

Cannes Film Festival

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

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.

Life photocall

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.

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.

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.