Unlike many of his contemporaries, we understand if Jake Gyllenhaal isn’t the first name that pops into your head when thinking of “stylish leading roles”. A career stretching from the tormented angst of Donnie Darko, to the drama of Brokeback Mountain and up to the super villainy of Mysterio in Spider-Man: Far From Home, Gyllenhaal has inhabited a wide range of character types with equally varied styles. If you’re sleeping on Gyllenhaal’s on-screen style, then you’re missing out on some top-tier cinematic inspiration.

As Gyllenhaal swings into the Marvel universe via the globetrotting Spider-Man blockbuster, we’ve gone back to examine Gyllenhaal’s most stylish silver screen appearances. Whether its playing tormented teens, intrepid reporters, or tragic cowboys, Gyllenhaal’s managed to solidify a cinematic wardrobe that can stand all on its own.

Tags: cowboys, cowboy-style, the-day-after-tomorrow, spiderman, spider-man, brokeback-mountain, donnie-darko, celebrity-style, reel-style, movie-style, movies, jake-gyllenhaal