12 Moments in Film That Changed the Way Men Dressed (for Better or for Worse)

The big screen is where fashions are immortalized. Not the runway, not the street.
IMAGE Channel Four Films

A stark difference between books and film is that the latter relies heavily on the visual medium; any cinephile will tell you that each onscreen element counts. Details such as a film’s color and lighting, props and, yes, a character’s sartorial choices could reveal much perspective on a motion picture.

Usually shaped by the trends and sensibilities of the film’s era, cinematic meaning aside, audiences take their style cues from fashion popularized on the silver screen—and the rest, as this list proves, is history.

Esquire navigates through the most stylish and definitive moments in films from the ‘40s to the ‘90s.


Citizen Kane
Year Released: 1941
Directed by: Orson Welles
Starring: Orson Welles, Joseph Cotten, Dorothy Comingore, Ray Collins

Although hardly a crime drama, Orson Welles’ 1941 masterpiece Citizen Kane provided much of the groundwork for the film noir genre that would later dominate the decade, with its stunning stylistics of stark lighting, harsh shadows and deep camera angles. An early reference for future noir heroes, Welles donned boxy suits, pinstriped jackets, ascot scarves and fedora hats — a fitting wardrobe for a publishing magnate spiraling downwards in his self-destruction, against the backdrop of the city’s corruption.


Year Released: 1942
Directed by: Michael Curtiz
Starring: Humphrey Bogart, Ingrid Bergman, Paul Henreid

When Humphrey Bogart uttered the line “Here’s looking at you, kid” in Casablanca, he introduced one of the most iconic appearances of the trench coat in history. Originally a military garment, Bogart gave the coat an air of sophistication as he starred alongside Ingrid Bergman in the bittersweet romance film.


Rebel Without a Cause
Year Released: 1955
Directed by: Nicholas Ray
Starring: James Dean, Natalie Wood, Sal Mineo

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When James Dean popped his collar and slicked his hair back in a pompadour, he ushered in a timeless definition of cool in Rebel Without a Cause. As the cool Jim Stark, he became the poster of youth rebellion, influencing angsty teenagers for decades to come. James Dean’s legacy will forever be immortalized in Lee 101 Riders.

An Affair to Remember
Year Released: 1957
Directed by: Leo McCarey
Starring: Cary Grant, Deborah Kerr

Lush and exquisite, An Affair to Remember is the pinnacle of romantic films in Hollywood. Cary Grant’s debonair charms defined the elegance and refinement of the 1950s, cementing his leading man status in mostly tuxedos and double-breasted suits.


A Hard Day’s Night
Year Released: 1964
Directed by: Richard Lester
Starring: John Lennon, Paul McCartney, George Harrison, Ringo Starr


The Beatles were iconic not just because of their sound, but with their distinct and uniform style that introduced London’s mod scene to the world. The fab four rocked mop hair, black turtlenecks, and bespoke monochromatic suits by tailor Dougie Millings.

Easy Rider
Year Released: 1969
Directed by: Dennis Hopper
Starring: Dennis Hopper, Peter Fonda, Jack Nicholson

Easy Rider demonstrated the free-spirited attitude of the 1960s in this biker film starring Peter Fonda, Dennis Hopper, and Jack Nicholson. Aboard American Chopper bikes while clad in fringe jackets and motorcycle boots, American counterculture doesn’t get more dead-on than this.


Year Released: 1975
Directed by: Hal Ashby
Starring: Warren Beatty, Julie Christie, Goldie Hawn


Tousled shag, ruffled open-collar shirts, and bell bottom denims — it’s like Warren Beatty was asked to dress himself in the excess-laden Shampoo, where he plays a lothario hairdresser caught up in the decade’s sexual revolution.

Saturday Night Fever
Year Released: 1977
Directed by: John Badham
Starring: John Travolta, Karen Lynn Gorney, Donna Pescow

Mention disco fashion to anyone, and John Travolta’s white three-piece suit immediately comes to mind. Even the actor’s famous disco pose is still one of today’s most revered pop culture references.


American Gigolo
Year Released: 1980
Directed by: Paul Schrader
Starring: Richard Gere, Hector Elizondo, Nina Van Pallandt, Bill Duke


Richard Gere spells casual elegance in American Gigolo, and it’s all thanks to Armani. Then an up-and-coming designer, Armani’s influence ushered in the Italian style revolution which introduced a more relaxed suit silhouette and the template for business casual with sports jackets and quarter zip pullover shirts.

Making The Grade
Year Released: 1984
Directed by: Dorian Walker
Starring: Judd Nelson, Dana Olsen

There’s not much to say about the cinematic merit of Making The Grade, a film on rich, entitled WASP youths in boarding school. The draped bright-hued sweaters and dandy patchwork pants, however, are spot-on elements of the preppy look, which renders this film more style than substance.


Boyz N The Hood
Year Released: 1991
Directed by: John Singleton
Starring: Cuba Gooding, Jr., Ice Cube, Larry Fishburne, Morris Chestnut, Angela Bassett, Nia Long


John Singleton’s semi-autobiographical film starring Ice Cube and Cuba Gooding about life in the hood set the precedent for today’s street style with baggy jeans, snapbacks, crew neck tees and sweatshirts.

Year Released: 1996
Directed by: Danny Boyle
Starring: Ewan McGregor, Ewen Bremmer, Jonny Lee Miller, Kevin McKidd, Robert Carlyle, Kelly Macdonald

Ewan McGregor is one of the world’s most formidable actors today, but back then he was a Scottish lad with a buzz cut that landed a breakout role as Mark Renton in a movie about delinquent youths on the streets of Edinburgh. Mark and his gang of fellow troubled teens deal with heroin addiction and evade authorities, all while dressed in “lived-in” outfits with elements of post-grunge, a style still channeled to this day.

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