19 Iconic Fashion Moments from Cinematic History

Taking a look back at some of the biggest films in Hollywood, here’s a roundup of the biggest fashion moments in cinematic history.

Fashion is one of the most memorable aspects of film. We all remember “that” scene from a film that marked cinema history. It could be a pivotal moment like Julia Roberts’s red dress, marking her Cinderella moment in Pretty Woman. Other times, it can influence high-fashion like Alicia Silverstone’s plaid suit in the ’90s teen dramedy Clueless. Cinema is a visual experience, and fashion heightens it. Let’s take a look.

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1. Gloria Swanson in Sunset Boulevard

“I’m ready for my closeup!” Gloria Swanson was the “it girl” of silent cinema. Later, she took on the role of an aging starlet in 1950’s Sunset Boulevard. Her infamous line and sequined gowns would make it her most memorable role throughout her career.

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2. Marilyn Monroe in Something’s Got to Give

Shots of Marilyn Monroe in Something’s Got to Give showcase her star quality. She was a beauty, with natural curves that costume designers wiggled into the tiniest dresses. It’s no wonder they became known as “wiggle dresses,” and Monroe became synonymous with the curvaceous look.

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3. Audrey Hepburn in How to Steal a Million

Audrey Hepburn was known for playing innocent ingénues onscreen in the 1950s. But, by the time the 1960s rolled around, she switched to playing the bad girl. In How To Steal A Million, her lace dress with matching mask became one of the film’s most memorable looks. It’ll also go down in history as cinema’s most dramatic “drinks after dinner” ensembles.

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4. Mia Farrow in Rosemary’s Baby

Mia Farrow’s pixie cut sparked a revolution of copycats after she debuted it in Rosemary’s Baby. The thriller also gave cinema a series of iconic images, such as this still of Farrow in a baby-blue nightgown. The sharp blade contrasts the sweet, child-like gown — a great representation of how fashion adds contrast and tension to a scene.

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5. Diane Keaton in Annie Hall

No list about cinema and fashion would be complete without Diane Keaton’s Annie Hall. Her interpretation of menswear — complete with a vest and tie — became one of cinema’s most iconic looks. It also sparked conversations about women’s style in the workplace. Her 1970s woman was a far cry from the skirt suits women wore in the workplace in the 1940s. Some could even say that Hall was one of cinema’s first fashion feminists.

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6. John Travolta in Saturday Night Fever

John Travolta’s dance moves made the girls swoon in Grease. In Saturday Night Fever, however, it wasn’t a high school, but rather a New York dance floor where he shined. Travolta played a working-class guy from Brooklyn who got loose at a disco. Shimming under the red lights, his white pants and matching vest became one of the greatest dance looks in film history.

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7. Diana Ross in Mahogany

Diana Ross, an actress and singer, has always exuded glamour and beauty. Her 1975 film, Mahogany, embodied that to its fullest. Playing a fashion design student, Ross wore a wardrobe that was set to stun. Her cream-colored ensembles and fluttering lashes helped cement Ross’s place as a style icon.

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8. Molly Ringwald in Pretty in Pink

Molly Ringwald was the pretty ’80s girl everyone could relate to. In Pretty In Pink, she played your average teen, trying to win her dream guy before the big school dance. Like Cinderella on her way to the ball, Ringwald was transformed into a beauty queen when she slipped on a pretty frock, inspiring girls around the world.

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9. David Bowie in Labyrinth

Few musicians have been as successful with their transformations as David Bowie. In the 1980s, he starred in the dark fantasy film Labyrinth, where he showed off his rock star look with big hair, bigger shoulder pads, and lots of sequins and ruffles. And, who could forget the eyeliner?

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10. Julia Roberts in Pretty Woman

Julia Roberts made a string of successful romantic comedies in the 1990s. One of the most memorable was her rags-to-riches story about a sex worker and her client in Pretty Woman. Julia’s transformation in the film hit its climax when she swept up her curls and slipped into a red, off-the-shoulder dress. Roberts even inspired a Barbie doll wearing a similar red dress after debuting her new look in the film.

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11. Cuba Gooding Jr. in Boyz n the Hood

Flat top haircuts, baggy jeans, and big necklaces were hallmarks of early ’90s hip-hop style. In 1991, Cuba Gooding Jr. brought the look to life in Boyz n the Hood. The film showed LA street style in a way that not only influenced high fashion at the time, but also made for an important piece of cinematic history.

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12. Alicia Silverstone in Clueless

Alicia’s Silverstone’s character Cher did more than simply popularize the term “As if.” She also made plaid suits and knee-high socks fashionable again. In 1995, Clueless sparked a television series and a generation of copycats vying for Cher’s California girl-vibe. Feather boas, mini slip dresses, and platform sandals were a few other fashion staples Cher made popular.

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13. Milla Jovovich in The Fifth Element

Since its debut in 1997, there’s never been a film quite like The Fifth Element. And, there’s never been a character quite like Milla Jovovich‘s Leeloo. In the beginning of the film, the audience is introduced to its heroine fleeing the police, skimpily dressed in a white tape getup and flaming orange hair. Her outfit became synonymous with the film and has since inspired countless Halloween costumes.

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14. Josh Hartnett in The Virgin Suicides

Josh Hartnett was a ’90s heartthrob. His natural good looks could make any outfit cool, including a full-on ’70s costume. When he appeared in Sofia Coppola’s The Virgin Suicides, he reaffirmed that when it comes to movies, bad boys wearing leather jackets and sunglasses will always win the girl.

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15. Zhang Ziyi in 2046

Director Wong Kar-Wai’s romantic drama 2046 was a visual treat for its artistic style and fashion influences. Borrowing elements from film noir, Zhang Ziyi plays the coquette Bai Ling, who glamorously sashays onto the screen in form-fitting dresses.

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16. Uma Thurman in Gattaca

In Gattaca, Uma Thurman plays a femme fatale opposite her (then) real-life lover, Ethan Hawke. With her smooth waves and glamorous dresses, she could coolly steal a man’s affections. And, with one film, she embodied the cool, blonde princess look of the 1990s.

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17. Keira Knightley in Atonement

One of the great love stories of the early aughts, 2007’s Atonement was a film that follows a couple as they endure the ups and downs of life during WWII. Before the war, Knightley’s character steps out in a silky green dress. Her onscreen presence sparked countless copies as women scrambled to look like the actress.

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18. Ryan Gosling in Drive

Ryan Gosling’s silent thriller Drive brought back ’80s nostalgia with an electro-synth soundtrack and an ultra-stylish wardrobe. His quiet hero drives the LA streets at night in a fitted metallic bomber, dark Levis, and leather gloves. It’s a swanky getup that makes him the coolest getaway driver in film history.

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19. Charlize Theron in Mad Max: Fury Road

With classic ’80s films like Ghostbusters and Terminator hitting the screens again in the 2010s, it was only a matter of time before Mad Max was remade. In 2015, the focus of the film Mad Max: Fury Road was on Charlize Theron‘s character, Furiosa, more so than Tom Hardy‘s character, Max. As a leading lady, her grit and style stole the screen. With a shaved head and a bionic arm, Furiosa’s look was a furious take on what a cyberpunk icon should look like.

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