Jake Gyllenhaal’s Style Evolution, from Donnie Darko to Tom Ford Heartthrob

Jake Gyllenhaal

Jake Gyllenhaal has come a long long way from his breakout leading role as a hot nerd in October Sky nearly 20 years ago. Over time, he left behind the roles that played on his boyish appeal, like as the title character in Donnie Darko, to take on complicated men in films as emotionally intense as Brokeback Mountain, for which he earned an Academy Award nomination, and Nightcrawler. With the evolution of his acting career, his personal style has also changed, slowly moving away from the casual ennui of Hollywood to embrace impeccably cut suits and ensembles, most recently by Tom Ford, the director of his latest film, Nocturnal Animals. In honor of Gyllenhaal’s 36th birthday, we’re taking a look back at the evolution of the heartthrob’s style evolution through the years.

May 1999
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18 year-old Jake received his first big Hollywood break in film ‘October Sky’. Here he was sighted outside of ‘Saturday Night Live’ in a very causal look featuring a denim jacket, plaid button up and blue slacks completed with a book bag.

November 2001
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At the Cachet’s One Year Anniversary, the young actor arrived in a more formal blazer and slacks look. He began to show his interest in mens style as he accessorized with a yellow wool scarf.

April 2002
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Remaining true to his relaxed youthful style, Jack attended the 9th Annual Kids for Kids Celebrity Carnival dressed in a pastel- stripped polo shirt, black over jacket, blue jeans and sneakers.

March 2003
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Not afraid of wearing a piece twice, Jake re-styled and rocked his pastel stripped polo under a blazer and paired with a dark blue jean and brown shoe for the 18th Annual IFP Independent Spirit Awards a year later.

July 2004
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Becoming accustom to mixing his casual pieces with formal on the red carpet, the actor opted for a white t-shirt, blazer and blue denim jeans for the LA premiere of ‘Donnie Darko’.

October 2005
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A more mature Jake was reveled at the 2005 premiere of ‘Jarhead’ in NYC. The featured actor posed on the red carpet in a black two-piece suit with a v-neck shirt and sweater combo underneath.

March 2006
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Jake looked dapper dressed in black tuxedo and bowtie at the 78th Annual Academy awards.

October 2007
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At the 2007 premiere of ‘Rendition’, Jake looked business-ready as he donned a light grey plaid suit, soft blue button up and burgundy tie on the red carpet. He completed his look with a pair of black leather shoes.

May 2010
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Dressed to perfection at the world premiere of his film ‘Prince of Persia’, Gyllenhaal opted for a classic three-piece black suite accessorized with a black tie and shoes.

November 2012
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A full bearded Gyllenhaal opted for a brown-on-brown double breasted ensemble for the New Eyes for the Needy 80th Anniversary Gala, where he was honored.

September 2014
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Jake donned a tailored blue suit with a black button-up at the 2014 premiere of his film ‘Nightcrawler’. He opted for a more casual brown boot to complete his look with a modern-relaxed touch.

September 2015
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The bachelor dropped jaws and sent girls hearts a flutter as he posed on the red carpet at the 2015 premiere of ‘Demolition’. His choice of wearing a tailored dark grey suit with the pairing of a burgundy tie and black detailed oxfords was perfect for the evening.

June 2014
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At the award winning actor arrived to the 70th annual Tony Awards rocking an incredibly rare double breasted tuxedo.

November 2016
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Stylishly dressed at the screening for his latest featured film ‘Nocturnal Animals’, Jake opted for a tailored navy blue suit, light blue button up, olive green tie and black leather shoes.