Gyllenhaal’s first leading role, October Sky is centered around the real life history of Homer Hickam Jr. Set in a coal town in West Virginia, Hickam defies his father’s wishes for his future and takes up rocketry, inevitably becoming a NASA engineer. Given that the film is set in the late-1950s, the style is fairly “traditional American.” Merging the two parts of Hickam’s life—a blue collar lineage and a nerdy obsession with rocket science—the character’s style could be described as “Carhartt meets Take Ivy”. A blend of barn jackets worn over dark jeans, camp collar shirts and faded flannels, workman’s chore coats and thick rimmed glasses all form the clean-cut, smart guy image you’d expect from a mid-century science geek. It may not be the most groundbreaking style of Gyllenhaal’s budding career, but it does show the actor’s ability to embody both teenage rebelliousness (albeit in a very reserved way here) and a “down-home” style that wouldn’t look out of place in middle America—be it mid-20th century, or in the present day.

Gyllenhall achieved his first taste of critical success with 2001 cult classic Donnie Darko. While a commercial failure—the film grossed just $7.5 million against a $4 million budget—following its Sundance debut Gyllenhall was suddenly recognized not only for his heartthrob qualities, but serious acting chops. Gyellenhall portrays the titular Donnie Darko, a high school teen who begins having visions of “Frank,” a mysterious man in a rabbit costume who claims he’s from the future. Throughout the film, Darko’s actions become increasingly erratic as Frank begins to influence his everyday life. Fearing for their son’s psychological well being, Darko’s parents ask him to visit a psychotherapist, who believes Darko displays tendencies of paranoid schizophrenia. The diagnosis causes Gyllenhall to rebel all the more, leading to a plot that embroils the entire town and eventually leads to Darko’s death. While the wardrobe is innocuous enough, Gyllenhall’s school uniform provides the perfect contrast to his manic tendencies in this off-kilter psychological thriller. The standout look, however, is no doubt Darko’s skeleton costume, which he wears during a Halloween party him and his sister host while their parents are out of town. While technically just a onesie beneath a heather gray hoodie, Darko’s ribcage shirt and bones bottoms inspired a generation of copycats, and interestingly enough aren’t too dissimilar from the Kapital skeleton pieces that everyone is currently lusting for.

While lambasted for its scientific inaccuracies, in the era of epic disaster films, The Day After Tomorrow managed to set itself apart due to its great cast—Dennis Quaid, Emmy Rossum, obviously Gyllenhall—and impressive special effects. Mostly set in (then) modern day Manhattan, the film follows climatologist Jack Hall (Quaid) and his son Sam (Gyllenhall), the former on a quest to save his son while the latter struggles to survive as one of three major arctic superstorms barrels through North America. The prodigy of a world-renowned scientist, Sam too is brilliant, visiting New York to compete in an academic decathlon. His wardrobe then, reflects his “charming nerd” nature, with looks ranging from a long corduroy jacket draped over a hoodie to a thick wool double breasted coat accessorized with a bright plaid scarf–all items perfectly suited for a high school senior with Ivy League ambitions. As the movie shifts into full-on disaster mode and the arctic chill sweeps over the city, Sam’s clothes transform into survival necessities, with the scarf doubling as a babushka-style head wrap and coat as a life-saving source of warmth. If The Day After Tomorrow accomplished anything over the past 15 years, it’s that Gyllenhall is a hell of a leading man, and looks damn good even in the eye of a planet-altering arctic typhoon.

If there’s one Jake Gyllenhaal movie that nearly everyone in your family knows about (even if they’ve not seen the film) it has to be Brokeback Mountain. Praised for it’s, at the time, pioneering approach to same-sex romance, the film went on to win several Oscars and international film awards. Following the lives of Ennis Del Mar (played by Heath Ledger) and Jack Twist (played by Gyllenhaal) as the pair connect, disconnect and reconnect over the years, the story’s setting—Wyoming, Texas and, broadly speaking, the “American West” in the late-1960s and ‘70s—help set the stage for the ultimately tragic, unresolved romance between the two male leads. From first impressions, both Del Mar and Twist embody the look and feel of run-of-the-mill ranchhands and cowboys; the pair meet working together as sheepherders in the Wyoming mountains. However, it’s Brokeback Mountain’s attempt to challenge the conventions of the masculine “cowboy” stereotype that makes its look at queer romance so resonant; one of Del Mar’s main fears is that, once his relationship with Twist is discovered—he’ll end up beaten and tortured by locals because of it. Of course, this easily recognizable aesthetic, coupled with the global resonance of the film, helped spur an interest in western fashion at the time. Gyllenhaal’s Jack Twist wears many of the trappings of cowboy fashion—from cowboy hats, roper boots and massive belt buckles—to more evergreen, casual pieces like snap-button shirts, chore coats, shearling jackets and durable denim. While the film is nearly 15 years old, you can still see the style today across the fashion spectrum. Ledger and Gyllenhaal’s Del Mar and Twist may look the Marlboro Man, their personal lives challenged the American standard.

Gyllenhaal is no stranger to portraying “cops who don’t play by convention,” and his work in Prisoners sees Gyllenhaal struggling with the emotional toil that goes into solving confounding, complex cases. Gyllenhaal walks that line with finesse the 2013 cop drama as Detective Loki, balancing the vengeful (and considering the circumstances, some might say righteous) anger of Keller Dover (played by Hugh Jackman) and the difficulties of remaining clear-headed and objective as a police officer. When Dover’s daughter is abducted and leads to her whereabouts grow thin, Dover takes justice into his own hands, capturing suspect Alex Jones (played by Paul Dano) and torturing him. As Dover attempts to find his missing daughter using vigilante justice, Loki sweats the story out from the perspective of a struggling detective, hitting dead end after dead end as the window to find the missing children grows smaller and smaller. While Prisoners is set in then-modern day Pennsylvania, the thick, tragic—almost colorless—atmosphere feels reminiscent of Christopher Nolan’s The Dark Knight. In Jones’ initial interrogation by police, Loki’s approach—always verging on violence—recalls Batman’s frustrated chat with The Joker after he’s captured by Gotham City PD. With slicked back hair, exposed tattoos and fully buttoned shirts (without a tie of course), Loki’s appearance is buttoned up in a literal sense, but is bursting at the seams with self-doubt, anxiety and desperation. Starting out by appearing as a fairly standard mystery thriller, Prisoners ultimately unravels in much the same way.

Easily one of Gyllenhall’s most intriguing roles, Nightcrawler was not only considered one of the year’s top films, but an important commentary on that state of cable news in an era that desperately needs it. The film focuses on Louis Bloom (Gyllenhall), a petty thief who after encountering a few photojournalists documenting a traffic accident, decides to become a Stringer—a freelance reporter who sells video clips of crime scenes to local news channels. Realizing that recordings of violent crimes in affluent white neighborhoods are highly lucrative, Gyllenhall begins using increasingly dubious tactics to capture the most graphic and obscene footage he can. Already a crook, Bloom’s blatant disregard for journalistic ethics—a recurring theme throughout the film—or his coworker's safety comes to a head when he begins staging crime scenes and withholding information from authorities in order to facilitate future business. An anti-hero in every sense of the word, Bloom beautifully toes the line between serial killer and entrepreneur, blackmailing a local news exec to sleep with him in one scene while letting his partner (Riz Ahmed) die in another without an inch of remorse. Although never actually specified, Bloom clearly harbors some sort of antisocial personality disorder, which his wardrobe adequately reflects. Pressed polos, slick drainpipe trousers, vintage leather jackets and straight laced suits all embody Bloom’s no-nonsense, emotionless demeanor—all business, without a glimmer of individuality. In a film with such a maniacally twisted, devious protagonist, Gyllenhall manages to make us cringe while still wondering where exactly he bought his watch. A performance that won’t soon be forgotten.

It’s hard to write a list compiling an actor’s most stylish on-screen appearances and not feature a movie helmed by designer-director Tom Ford. Nocturnal Animals—Ford’s second film after A Single Man—is more of a mood than a narrative, even though it actually features a story within its story. As Susan Morrow (played by Amy Adams) reads through her ex-husband, Edward Sheffield’s (played by Gyllenhaal), manuscript, the audience experiences two stories: The deterioration of her relationship with Sheffield in the real world, and the tragedy of Tony Hastings (also played by Gyllenhaal) in the world of the novel. While Gyllenhaal’s style when playing Sheffield is fairly bog standard, it’s his looks as Hastings that embody Tom Ford’s penchant for aesthetic shine. Shrouding the novel’s sunny Western scenes in a foreboding emotional darkness, Gyllenhaal’s beleaguered, grieving character manages to embody the American everyman, as well as a warped look at the strongman sensibilities of Western and cowboy clothing (especially contrasted with Michael Shannon’s Detective Andes). Like Ford’s earlier cinematic work, aesthetics and tone stretch beyond the clothing worn on the characters, making his films dripping with ambience physically and emotionally. It’s that tense ambience and tone that make Gyllenhaal’s two characters—especially Hastings—exceedingly memorable.