1950s: James Dean as Jim Stark, Rebel Without a Cause (1955)
There's no better way to start than with the epitome of cool himself, Mr. James Dean. There's a reason that pained grimace peers down from college dorm rooms across the country, perfectly framed by the popped collar of a red jacket—easily one of the most iconic pieces of clothing in cinema history.
Honorable Mentions: Elvis Presley in Jailhouse Rock (1957) and Jean-Pierre Léaud in The 400 Blows (1959)
1960s: Dustin Hoffman as Benjamin Braddock, The Graduate (1967)
Your eye might be drawn to that stockinged leg in the poster’s foreground, but Hoffman's cool, all-American look deserves attention of its own. With his quirky suits and simple black polo shirt—a wardrobe that is quite possibly the inspiration for every Band of Outsiders collection ever—Hoffman exudes just the right ebullience as a naïve, optimistic young adult trying to figure out his way.
Honorable Mentions: Jean-Paul Belmondo in Breathless (1960) and Richard Beymer in West Side Story (1961)
1970s: Dennis Quaid as Mike, Breaking Away (1979)
The movie may be about competitive cycling, but fortunately there's not much Lycra to be found in this summer classic about four small-town friends just out of high school. Quaid's Mike is the group's top dog, roaming the streets in tight t-shirts and a floppy mop of sun-bleached hair. It's a testament to his easygoing style that he even manages to pull off a pair of cutoff jean shorts.
Honorable Mentions: Ryan O'Neal in Love Story (1970) and Michael Beck in The Warriors (1979)
1980s: Spike Lee as Mookie, Do the Right Thing (1989)
Though his personal style isn’t at the forefront of this serious and incisive film about race relations, Mookie’s flattop, Dodgers jersey, and chain have become emblematic of the film's Bed-Stuy setting. His outfit, along with the Air Jordans he and his friends wear in the film, also served as an introduction for many viewers to New York's nascent hip-hop culture.
Honorable Mentions: Tom Cruise in Risky Business (1983) and Judd Nelson in The Breakfast Club (1985)
1990s: Jason Schwartzman as Max Fischer in Rushmore (1998)
Wes Anderson's second feature film already displayed many of the hallmarks of his developing style, especially a careful eye for sartorial details. Schwartzman plays the eccentric Max Fischer, purposefully awkward in his too-tight suit, nerd glasses, and bright-red beret. Little did any of us know that fifteen years later, we'd all be dressing a little bit like him.
Honorable Mentions: Edward Clements in Metropolitan (1990) and Leonardo DiCaprio in Romeo + Juliet (1996)
2000s: Joseph Gordon-Levitt, (500) Days of Summer (2009)
A romantic comedy for guys who don't like romantic comedies, (500) Days of Summer is the postmodern answer to every Julia Roberts movie your girlfriend ever made you sit through. Gordon-Levitt is a picture-perfect millennial, down to his skinny ties, sweater vests, and messenger bag, unsure of his way in life and willfully blinded by optimism.
Honorable Mentions: Gael García Bernal and Diego Luna in Y Tu Mamá También (2001) and Kieran Culkin in Igby Goes Down (2002)