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 , for which he earned an Academy Award nomination, and Brokeback Mountain 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, . 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. Nocturnal Animals
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.
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.
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.
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.
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’.
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.
Jake looked dapper dressed in black tuxedo and bowtie at the 78th Annual Academy awards.
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.
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.
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.
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.
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.
At the award winning actor arrived to the 70th annual Tony Awards rocking an incredibly rare double breasted tuxedo.
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.