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19 Iconic Fashion Moments from Cinematic History

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.


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.

19 Iconic Fashion Moments from Cinematic History — William Holden and Gloria Swanson in Sunset Boulevard
William Holden and Gloria Swanson in Sunset Boulevard (1950). Directed by Billy Wilder. Paramount USA scene still. Photo by Paramount/Kobal/Shutterstock.
19 Iconic Fashion Moments from Cinematic History — Erich von Stroheim and Gloria Swanson in Wilder's Sunset Boulevard
Erich von Stroheim and Gloria Swanson in Sunset Boulevard (1950). Directed by Billy Wilder. Paramount USA scene still. Photo by G E Richardson/Paramount/Kobal/Shutterstock.
19 Iconic Fashion Moments from Cinematic History — Erich von Stroheim, Gloria Swanson, and William Holden in Sunset Boulevard
Erich von Stroheim, Gloria Swanson, and William Holden in Sunset Boulevard (1950). Directed by Billy Wilder. Paramount USA film portrait. Photo by Paramount/Kobal/Shutterstock.

2. Marilyn Monroe in Something’s Got to Give

19 Iconic Fashion Moments from Cinematic History — Marilyn Monroe in Something's Got to Give
Marilyn Monroe in Something’s Got to Give (1962). Directed by George Cukor. 20th Century Fox USA film portrait. Photo by 20th Century Fox/Kobal/Shutterstock.
19 Iconic Fashion Moments from Cinematic History — Marilyn Monroe's Black Dress from Something's Got to Give
Marilyn Monroe in Something’s Got to Give (1962). Directed by George Cukor. 20th Century Fox USA film portrait. Photo by 20th Century Fox/Kobal/Shutterstock.
19 Iconic Fashion Moments from Cinematic History — Marilyn Monroe's Curvaceous Look  in Something's Got to Give
Marilyn Monroe in Something’s Got to Give (1962). Directed by George Cukor. 20th Century Fox USA film portrait. Photo by 20th Century Fox/Kobal/Shutterstock.

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.


3. Audrey Hepburn in How to Steal a Million

19 Iconic Fashion Moments from Cinematic History — Audrey Hepburn's Iconic Black Dress in How to Steal a Million
Audrey Hepburn in How to Steal a Million (1966). Directed by William Wyler. 20th Century Fox USA film portrait. Photo by 20th Century Fox/Kobal/Shutterstock.
19 Iconic Fashion Moments from Cinematic History — Audrey Hepburn in Simpler Clothes in How to Steal a Million
Audrey Hepburn in How to Steal a Million (1966). Directed by William Wyler. 20th Century Fox USA scene still. Photo by 20th Century Fox/Kobal/Shutterstock.
19 Iconic Fashion Moments from Cinematic History — Audrey Hepburn in How to Steal a Million
Audrey Hepburn in How to Steal a Million (1966). Directed by William Wyler. 20th Century Fox USA scene still. Photo by 20th Century Fox/Kobal/Shutterstock.

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.


4. Mia Farrow in Rosemary’s Baby

19 Iconic Fashion Moments from Cinematic History — Mia Farrow's Blue Nightgown in Rosemary's Baby
Mia Farrow in Rosemary’s Baby (1968). Directed by Roman Polanski. Paramount USA scene still. Photo by Paramount/Kobal/Shutterstock.
19 Iconic Fashion Moments from Cinematic History — Mia Farrow's Pixie Cut in Rosemary's Baby
Mia Farrow in Rosemary’s Baby (1968). Directed by Roman Polanski. Paramount USA scene still. Photo by Paramount/Kobal/Shutterstock.

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.


5. Diane Keaton in Annie Hall

19 Iconic Fashion Moments from Cinematic History — Diane Keaton and Woody Allen in Annie Hall
Diane Keaton and Woody Allen in Annie Hall (1977). Directed by Woody Allen. United Artists USA scene still. Photo by Rollins-Joffe/United Artists/Kobal/Shutterstock.
19 Iconic Fashion Moments from Cinematic History — Woody Allen and Diane Keaton in Annie Hall
Woody Allen and Diane Keaton in Annie Hall (1977). Directed by Woody Allen. United Artists USA scene still. Photo by Rollins-Joffe/United Artists/Kobal/Shutterstock.
19 Iconic Fashion Moments from Cinematic History — Diane Keaton Modernizing Women's Wear in Annie Hall
Diane Keaton in Annie Hall (1977). Directed by Woody Allen. United Artists USA scene still. Photo by Rollins-Joffe/United Artists/Kobal/Shutterstock.

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.


6. John Travolta in Saturday Night Fever

19 Iconic Fashion Moments from Cinematic History — John Travolta in the Iconic White Suit in Saturday Night Fever
John Travolta in Saturday Night Fever (1977). Directed by John Badham. Paramount USA scene still. Photo by Paramount/Kobal/Shutterstock.
19 Iconic Fashion Moments from Cinematic History — Karen Lynn Gorney and John Travolta in Saturday Night Fever
Karen Lynn Gorney and John Travolta in Saturday Night Fever (1977). Directed by John Badham. Paramount USA scene still. Photo by Paramount/Kobal/Shutterstock.
19 Iconic Fashion Moments from Cinematic History — John Travolta in Saturday Night Fever
John Travolta in Saturday Night Fever (1977). Directed by John Badham. Paramount USA scene still. Photo by Paramount/Kobal/Shutterstock.

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.


7. Diana Ross in Mahogany

19 Iconic Fashion Moments from Cinematic History — Diana Ross in Mahogany
Diana Ross in Mahogany (1975). Directed by Berry Gordy. Paramount USA film portrait. Photo by Paramount/Kobal/Shutterstock.
19 Iconic Fashion Moments from Cinematic History — Diana Ross Strikes a Stunning Figure in Mahogany
Diana Ross in Mahogany (1975). Directed by Berry Gordy. Paramount USA film portrait. Photo by Paramount/Kobal/Shutterstock.

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.


8. Molly Ringwald in Pretty in Pink

19 Iconic Fashion Moments from Cinematic History — Molly Ringwald in Pretty In Pink
Molly Ringwald in Pretty In Pink (1986). Directed by Howard Deutch. Paramount USA film portrait. Photo by Paramount/Kobal/Shutterstock.
19 Iconic Fashion Moments from Cinematic History — Andrew McCarthy, Molly Ringwald, and Jon Cryer in Pretty In Pink
Andrew McCarthy, Molly Ringwald, and Jon Cryer in Pretty In Pink (1986). Directed by Howard Deutch. Paramount USA scene still. Photo by Paramount/Kobal/Shutterstock.
19 Iconic Fashion Moments from Cinematic History — Molly Ringwald's 80s Fashion in Pretty In Pink
Molly Ringwald in Pretty In Pink (1986). Directed by Howard Deutch. Paramount USA film portrait. Photo by Paramount/Kobal/Shutterstock.

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.


9. David Bowie in Labyrinth

19 Iconic Fashion Moments from Cinematic History — David Bowie in Labyrinth
David Bowie in Labyrinth (1986). Directed by Jim Henson. Jim Henson Productions USA film portrait. Photo by Jim Henson Productions/Kobal/Shutterstock.
19 Iconic Fashion Moments from Cinematic History — David Bowie as The Goblin King in Labyrinth
David Bowie in Labyrinth (1986). Directed by Jim Henson. Jim Henson Productions USA film portrait. Photo by Jim Henson Productions/Kobal/Shutterstock.

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?


10. Julia Roberts in Pretty Woman

19 Iconic Fashion Moments from Cinematic History — Richard Gere and Julia Roberts in Pretty Woman
Richard Gere and Julia Roberts in Pretty Woman (1990). Directed by Garry Marshall. Touchstone Pictures USA scene still. Photo by Touchstone/Kobal/Shutterstock.
19 Iconic Fashion Moments from Cinematic History — Julia Roberts in Pretty Woman
Julia Roberts in Pretty Woman (1990). Directed by Garry Marshall. Touchstone Pictures USA scene still. Photo by Touchstone/Kobal/Shutterstock.
19 Iconic Fashion Moments from Cinematic History — Julia Roberts' Iconic Looks in Pretty Woman
Julia Roberts in Pretty Woman (1990). Directed by Garry Marshall. Touchstone Pictures USA scene still. Photo by Touchstone/Kobal/Shutterstock.

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.


11. Cuba Gooding Jr. in Boyz n the Hood

19 Iconic Fashion Moments from Cinematic History — Morris Chestnut, Cuba Gooding Jr., and Ice Cube in Boyz n the Hood
Morris Chestnut, Cuba Gooding Jr., and Ice Cube in Boyz n the Hood (1991). Directed by John Singleton. Columbia USA film portrait. Photo by Columbia/Kobal/Shutterstock.
19 Iconic Fashion Moments from Cinematic History — Nia Long and Cuba Gooding Jr. in Boyz n the Hood
Nia Long and Cuba Gooding Jr. in Boyz n the Hood (1991). Directed by John Singleton. Columbia USA film portrait. Photo by Columbia/Kobal/Shutterstock.
19 Iconic Fashion Moments from Cinematic History — Ice Cube, Cuba Gooding Jr., and Morris Chestnut in Boyz n the Hood
Ice Cube, Cuba Gooding Jr., and Morris Chestnut in Boyz n the Hood (1991). Directed by John Singleton. Columbia USA film portrait. Photo by Columbia/Kobal/Shutterstock.

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.


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.

19 Iconic Fashion Moments from Cinematic History — Stacey Dash and Alicia Silverstone in Clueless
Stacey Dash and Alicia Silverstone in Clueless (1995). Directed by Amy Heckerling. Paramount USA scene still. Photo by Paramount/Kobal/Shutterstock.
19 Iconic Fashion Moments from Cinematic History — Alicia Silverstone and Stacey Dash Serving Looks in Clueless
Alicia Silverstone and Stacey Dash in Clueless (1995). Directed by Amy Heckerling. Paramount USA scene still. Photo by Paramount/Kobal/Shutterstock.
19 Iconic Fashion Moments from Cinematic History — Alicia Silverstone in Clueless
Alicia Silverstone in Clueless (1995). Directed by Amy Heckerling. Paramount USA scene still. Photo by Paramount/Kobal/Shutterstock.

13. Milla Jovovich in The Fifth Element

19 Iconic Fashion Moments from Cinematic History — Milla Jovovich and Ian Holm in The Fifth Element
Milla Jovovich and Ian Holm in The Fifth Element (1997). Directed by Luc Besson. Columbia/Tri-Star France scene still. Photo by Columbia/Tri-Star/Kobal/Shutterstock.
19 Iconic Fashion Moments from Cinematic History — Milla Jovovich's Sci-fi Style in The Fifth Element
Milla Jovovich in The Fifth Element (1997). Directed by Luc Besson. Columbia/Tri-Star France scene still. Photo by Columbia/Tri-Star/Kobal/Shutterstock.
19 Iconic Fashion Moments from Cinematic History — Milla Jovovich in The Fifth Element
Milla Jovovich in The Fifth Element (1997). Directed by Luc Besson. Columbia/Tri-Star France film portrait. Photo by Columbia/Tri-Star/Kobal/Shutterstock.

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.


14. Josh Hartnett in The Virgin Suicides

19 Iconic Fashion Moments from Cinematic History — Josh Hartnett in The Virgin Suicides
Josh Hartnett in The Virgin Suicides (1999). Directed by Sofia Coppola. American Zoetrope USA scene still. Photo by American Zoetrope/Kobal/Shutterstock.
19 Iconic Fashion Moments from Cinematic History — Kirsten Dunst and Josh Hartnett in The Virgin Suicides
Kirsten Dunst and Josh Hartnett in The Virgin Suicides (1999). Directed by Sofia Coppola. American Zoetrope USA scene still. Photo by American Zoetrope/Kobal/Shutterstock.

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.


15. Zhang Ziyi in 2046

19 Iconic Fashion Moments from Cinematic History — Zhang Ziyi in 2046
Zhang Ziyi in 2046 (2004). Directed by Wong Kar-Wai. Columbia/Block 2/Jet Tone Films China/Hong Kong/France/Germany scene still. Photo by Wing Shya/Columbia/Jet Tone/Kobal/Shutterstock.
19 Iconic Fashion Moments from Cinematic History — Zhang Ziyi's Bodycon Waedrobe in 2046
Zhang Ziyi in 2046 (2004). Directed by Wong Kar-Wai. Columbia/Block 2/Jet Tone Films China/Hong Kong/France/Germany scene still. Photo by Wing Shya/Columbia/Jet Tone/Kobal/Shutterstock.

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.


16. Uma Thurman in Gattaca

19 Iconic Fashion Moments from Cinematic History — Uma Thurman's Ice Princess Look in Gattaca
Uma Thurman in Gattaca (1997). Directed by Andrew Niccol. Columbia USA scene still. Photo by Columbia/Kobal/Shutterstock.
19 Iconic Fashion Moments from Cinematic History — Uma Thurman's Scifi Office Wear in Gattaca
Uma Thurman in Gattaca (1997). Directed by Andrew Niccol. Columbia USA scene still. Photo by Columbia/Kobal/Shutterstock.
19 Iconic Fashion Moments from Cinematic History — Uma Thurman in Gattaca
Uma Thurman in Gattaca (1997). Directed by Andrew Niccol. Columbia USA scene still. Photo by Columbia/Kobal/Shutterstock.

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.


17. Keira Knightley in Atonement

19 Iconic Fashion Moments from Cinematic History — Keira Knightley's Striking Green Dress in Atonement
Keira Knightley in Atonement (2007). Directed by Joe Wright. Focus Features UK/France scene still. Photo by Focus/Kobal/Shutterstock.
19 Iconic Fashion Moments from Cinematic History — Keira Knightley in Atonement
Keira Knightley in Atonement (2007). Directed by Joe Wright. Focus Features UK/France scene still. Photo by Focus/Kobal/Shutterstock.
19 Iconic Fashion Moments from Cinematic History — Keira Knightley Wears a Classic Bathing Suit in Atonement
Keira Knightley in Atonement (2007). Directed by Joe Wright. Focus Features UK/France scene still. Photo by Focus/Kobal/Shutterstock.

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.


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.

19 Iconic Fashion Moments from Cinematic History — Ryan Gosling's Full Ensemble in Drive
Ryan Gosling in Drive (2011). Directed by Nicolas Winding Refn. Bold Films USA scene still. Photo by Bold Films/Kobal/Shutterstock.
19 Iconic Fashion Moments from Cinematic History — Ryan Gosling's Scorpion Jacket in Drive
Ryan Gosling in Drive (2011). Directed by Nicolas Winding Refn. Bold Films USA scene still. Photo by Bold Films/Kobal/Shutterstock.
19 Iconic Fashion Moments from Cinematic History — Ryan Gosling in Drive
Ryan Gosling in Drive (2011). Directed by Nicolas Winding Refn. Bold Films USA scene still. Photo by Bold Films/Kobal/Shutterstock.

19. Charlize Theron in Mad Max: Fury Road

19 Iconic Fashion Moments from Cinematic History — Charlize Theron in Mad Max: Fury Road
Charlize Theron in Mad Max: Fury Road (2015). Directed by George Miller. Village Roadshow Austrailia film portrait. Photo by Jasin Boland/Village Roadshow/Kobal/Shutterstock.
19 Iconic Fashion Moments from Cinematic History — Charlize Theron's Cyberpunk Chic in Mad Max: Fury Road
Charlize Theron in Mad Max: Fury Road (2015). Directed by George Miller. Village Roadshow Austrailia film portrait. Photo by Jasin Boland/Village Roadshow/Kobal/Shutterstock.
19 Iconic Fashion Moments from Cinematic History — Abbey Lee Kershaw, Courtney Eaton, Zoe Kravitz, Charlize Theron, and Riley Keough in Mad Max: Fury Road
Abbey Lee Kershaw, Courtney Eaton, Zoe Kravitz, Charlize Theron, and Riley Keough in Mad Max: Fury Road (2015). Directed by George Miller. Village Roadshow Austrailia film portrait. Photo by Jasin Boland/Village Roadshow/Kobal/Shutterstock.

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.


Want more in fashion and cinema history? Check out these photo tours through the Shutterstock archives.

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