Twentieth Century Fox
25 iconic outfits from film history
Marilyn Monroe in a scene from ‘Gentlemen Prefer Blondes.’
Costuming is one of the most unsung aspects of the movie industry. For the most part, when it’s done right, the viewer hardly even notices it. A beautiful, period-appropriate, Gilded Age gown, for example, only helps sink the viewer further into a story about the turn of the 20th-century woman. It’s when the costuming is done poorly, when it doesn’t match the time and space and pulls us from the world, that we tend to take note of it.
Once in a while, however, an outfit stands out for all the right reasons. Maybe a certain outfit perfectly encapsulates a character’s identity. Or it’s just a stunning, well-crafted piece of clothing. Or maybe the ensemble inspires trends beyond the cinema and begins to affect how we dress in real life (a la “Bridgerton” costumes).
To celebrate these outstanding moments in costuming, Stacker dug into fashion in film history to highlight 25 of the most iconic outfits ever to grace the silver screen. From Audrey Hepburn’s “Breakfast at Tiffany’s” dress to Uma Thurman’s “Kill Bill” getup and everything in between, these looks live in our minds rent-free.
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Audrey Hepburn’s little black dress
Audrey Hepburn looks into a window a Tiffany’s in a still from the film ‘Breakfast at Tiffany’s.’
Say what you will about Holly Golightly’s morals, but there’s no denying the “Breakfast at Tiffany’s” socialite was an absolute fashion plate. Her most iconic outfit comes right at the film’s start—the “little black dress” she pairs with pearls, a croissant, and a cup of takeout coffee to look at Tiffany’s window displays.
Designed by Hubert de Givenchy, the dress is made of Italian silk and has been described as a perfect example of 1960s fashion—chic, delicate, sensual, and Parisian. All told, there were three versions of the dress: one that sits in Givenchy’s archives, one in a Madrid museum, and one that sold to a private collector at auction for $800,000 in 2007.
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Grace Kelly’s white, strapless gown
Grace Kelly in ‘To Catch a Thief.’
In Grace Kelly’s third and final collaboration with Alfred Hitchcock, she dons the most iconic costume of their partnership—a white, strapless organza dress accessorized with an elaborate diamond necklace. Worn in 1995’s “To Catch a Thief,” the dress was designed by costumer Edith Head, who had worked with Hitchcock on many of his other films. While the actress-turned-princess throws on the gown to watch fireworks from her hotel room with her love interest (who is also a suspected cat burglar), modern designers have recreated the timeless dress for a much bigger occasion: your wedding day.
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Marilyn Monroe’s white subway grate dress
Marilyn Monroe in a scene from ‘The Seven Year Itch.’
Costume designer William Travilla’s white cocktail dress for Marilyn Monroe’s role in “The Seven Year Itch” is arguably the most iconic clothing item she’s ever worn. If nothing else, the shot of her attempting to hold down the draped skirt as it billows around her due to the whoosh of a subway train is one of Hollywood’s defining images.
According to Hollywood lore, Monroe’s then-husband, Joe DiMaggio, stormed off set after seeing the scene filmed, feeling that the dress was too revealing—and while we may not bat an eye at it now, it definitely showed a lot of leg for 1955. In 2011, the dress sold at auction for $4.6 million.
Sharon Stone’s icy white interrogation dress
Sharon Stone in a scene from ‘Basic Instinct.’
The film “Basic Instinct” is widely praised for the groundbreaking way it depicts sex and sexuality. A prime example of this revolutionary approach is the dress Sharon Stone’s Catherine Tramell wears—or, rather, what she doesn’t wear—while under police interrogation. The white, high-necked, sleeveless dress she dons was designed to allow Stone to sit and move like a man, acting decisions that felt very in line with the essence of the character. In 2022, Stone told InStyle that she’d kept the dress but hadn’t tried it on since filming wrapped.
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Olivia Newton-John’s black spandex pants
Olivia Newton-John and John Travolta in a scene from ‘Grease.’
The high-waisted spandex pants Olivia Newton-John wears in the final scenes of “Grease” were already vintage when the film was shot in 1977 and released the following year. They were so tight that, according to Vogue, she had to be sewn into them each morning and could barely move without fearing split seams.
In 2019, the actress auctioned off both the pants and the matching leather jacket to raise money for cancer research. Together, the items sold for $405,700, though the buyer returned the jacket to Newton-John just days later, saying it rightfully belonged to her and shouldn’t be relegated to some billionaire’s collection for bragging rights.
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Reese Witherspoon’s pink Jackie O look
Reese Witherspoon in ‘Legally Blonde 2: Red, White & Blonde.’
Before filming began on “Legally Blonde,” costume designer Sophie De Rakoff visited several sororities around Los Angeles to get a feel for what colors college-age girls were gravitating toward. She was searching for a signature color for Elle Woods and, after her visits, said she realized it just had to be pink. The color carries over into “Legally Blonde 2: Red, White & Blonde,” where Reese Witherspoon dons this Jackie O-inspired look.
The actress reportedly had it written into her contract that she could keep every one of the outfits she wore in the second film, so, as far as we know, this iconic getup is still taking up space in the back of one of her closets.
Warner Home Video
Judy Garland’s Dorothy dress
Judy Garland in ‘The Wizard of Oz.’
If you’re at all familiar with the making of “The Wizard of Oz,” you’re probably well aware of the fact that several pairs of Dorothy’s ruby slippers have disappeared since the film wrapped in 1939. What you may not know is that her blue-and-white gingham dress was also lost for years.
It was only rediscovered in 2021 when the Catholic University of America (to which the dress was donated back in the 1970s) was doing a major cleanout of its drama department and found it tucked away in an unassuming bag. The pinafore’s color was reportedly chosen so it would pop against Oz’s other vibrant colors, and the straps, according to a Smithsonian expert, show signs of being mended over and over, indicating that Garland frequently ripped the costume during shooting.
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Madonna’s eclectic vintage look
Madonna on the set of ‘Desperately Seeking Susan.’
Susan Seidelman, the director of “Desperately Seeking Susan,” said Madonna won the role of the film’s main character, a grifter named Susan, because she embodied 1980s downtown Manhattan. This is why Seidelman and costume director Santo Loquasto dug through the pop star’s closet for wardrobe inspiration.
The character Susan’s jacket, a cropped tuxedo fit with gold mosaic lapels and a bedazzled pyramid emblem on the back, wasn’t pulled directly from Madonna’s private collection the way other costume pieces were, but it sounds as if it could have been. In 2016, the iconic garment sold for $87,500 at auction.
Alicia Silverstone’s yellow plaid suit
Alicia Silverstone and Stacey Dash in a scene from ‘Clueless.’
According to Alicia Silverstone, who played Cher Horowitz in “Clueless,” the costume designer had three color options for the Dolce & Gabbana plaid suit she wears near the film’s beginning. Ultimately, they decided to go with yellow because they felt it was most appropriate for the scene. As for where the suit is today, Silverstone tells Vogue no one knows; it’s been lost to the annals of Hollywood.
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Julia Roberts’ red gown and white gloves
Julia Roberts and Richard Gere in a scene from ‘Pretty Woman.’
Vivian Ward’s outfits in “Pretty Woman” tell the story of a woman on a journey. At the beginning of the film, her clothes are more revealing and look cheaply made, but by the time the opera scene happens—where she dons this stunning red evening gown—she’s started to dress more demurely, like a “real lady.”
The costume is just sexy enough, however, with its off-the-shoulder sweetheart neckline and sky-high slit, to assure the viewer Vivian hasn’t totally lost sight of herself. According to costume designer Marilyn Vance, producers initially wanted the dress to be black, but she convinced them that red was the way to go.
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Maggie Cheung’s rose-covered cheongsam
Maggie Cheung in a scene from ‘In the Mood for Love.’
The clothing in “In the Mood for Love” is so critical to the storytelling that it’s essentially its own character. The film’s costumer, William Chang, designed 50 cheongsams (which were very popular in 1960s Hong Kong, having descended from the robes Qing dynasty women had worn for centuries) for Maggie Cheung, though she only wore about 30 of them. The multicolored, rose-covered cheongsam pops up at the film’s climax when Cheung and Tony Leung Chiu-wai’s characters confess their love for one another.
Cineteca di Bologna
Anita Ekberg’s fountain gown
Anita Ekberg in ‘La Dolce Vita.’
“La Dolce Vita” introduced the world to Italian fashion—clean, simple clothes that flattered the wearer’s figure rather than overshadowing it. The black strapless gown Anita Ekberg’s character, Sylvia, wears as she frolics in the Trevi Fountain is a perfect example of this. Designed by the Fontana sisters, the dress is featured front and center on the film’s poster.
Diana Ross’ tangerine kimono
Diana Ross in ‘Mahogany.’
Legend has it that Diana Ross, who both starred in and designed the costumes for “Mahogany,” took eight months to come up with all 50 of her character’s looks. While many of the outfits are over-the-top and campy, some scholars have argued that they helped address the bias many held against flashy and brightly colored clothing, which, at the time, was largely worn by women of color and seen as cheap or of bad taste. The tangerine kimono in question is worn by Ross while she walks a runway and is adorned with a sequined Chinese-style dragon across the front.
Vivien Leigh’s curtains from the window
Clark Gable and Vivien Leigh in a scene from ‘Gone with the Wind.’
Back in 2010, the University of Texas raised $30,000 to restore the green “curtain” dress Vivien Leigh wore as Scarlett O’Hara in the 1939 film “Gone with the Wind.” In the movie, Scarlett tears down the curtains in her living room and uses the material to make a dress meant to impress Rhett Butler. In real life, the gown wasn’t made of actual curtains but of green velvet treated to look aged and sun-worn. Some 70 years later, the dress was literally falling apart at the seams because, as one conservationist told NPR, it was only made to last for as long as it took to film the movie.
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Paramount Home Entertainment
Sarah Jessica Parker’s wedding gown
Kim Cattrall, Sarah Jessica Parker, Kristin Davis, and Cynthia Nixon in ‘Sex and the City.’
At the outset of “Sex and the City: The Movie,” Sarah Jessica Parker’s Carrie Bradshaw heads downtown to marry Mr. Big. The wedding doesn’t happen, of course, but the enormous Vivienne Westwood gown she wore stuck in audiences’ minds nonetheless. It was so legendary that, according to Glamour, a knock-off version of the dress reportedly sold out within hours of being released.
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Lisa Kudrow and Mira Sorvino’s metallic minis
Lisa Kudrow and Mira Sorvino at party in a scene from the film ‘Romy And Michele’s High School Reunion.’
The maximalist style in “Romy and Michele’s High School Reunion” is iconic across the board, but the pink and blue metallic minidresses Lisa Kudrow and Mia Sorvino’s characters wear near the end of the movie really stand out. Ironically, the fashion moment almost didn’t happen.
The film’s costume designer, Mona May, had originally planned to put Kudrow in a flowy, pink chiffon number, but the comedian pushed for something that looked more like Sorvino’s outfit to illustrate the friends’ closeness and unity.
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Diane Keaton’s menswear mashup
Diane Keaton and Woody Allen in the film ‘Annie Hall.’
Woody Allen had so much faith in Diane Keaton’s ability to portray Annie Hall that he gave her almost free rein to compose the character exactly how she wanted; that included creating Annie’s costumes. The classic menswear mashup she wears in one of the film’s first scenes was entirely Keaton’s own creation and was very much a play on her personal sense of style.
Rumor has it that the “Annie Hall” costume designer, Ruth Morley, hated many of the outfits Keaton put together, including this one, but we’re glad Allen overruled her—the costume inspired an entire movement in women’s fashion.
Whitney Houston’s futuristic stage costume
Whitney Houston in a scene from ‘The Bodyguard.’
When Susan Nininger was tapped to create the costumes for “The Bodyguard,” it was the first major film she had ever worked on. While the pressure may have been too much for some, she certainly rose to the occasion and created one of the most iconic outfits in all of film history—Whitney Houston’s futuristic performance costume.
In a clip celebrating the 30th anniversary of the film, Nininger revealed the outfit was inspired by the movie “Metropolis” and the breastplates designer Thierry Mugler made at the time. In 2018, the costume, which Nininger admitted was super difficult for Houston to wear because of its complexity, went up for auction with a starting bid of $10,000.
Kate Winslet’s sequined gown
Kate Winslet and Leonardo DiCaprio in a scene from ‘Titanic.’
When Jack first stumbles upon Rose in the 1997 blockbuster “Titanic,” she’s wearing this iconic red-and-black sequined dress and preparing to throw herself over the side of the ship, fed up with living life in a gilded cage. He talks her down, of course, and one of cinema’s greatest love stories begins.
Designed by Deborah Lynn Scott (who won an Oscar for her costume work in the movie), the dress was made in multiples so that the necessary stunts could be completed. The design involved a lot of intricate beading, as was popular with evening gowns at the time. In 2012, the dress sold for $330,000 at a movie memorabilia auction.
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Uma Thurman’s black-and-yellow tracksuit
Uma Thurman in ‘Kill Bill: Vol. 1.’
Uma Thurman’s skintight black-and-yellow tracksuit from “Kill Bill” might be a favorite Halloween costume among 20-something women, but the actress reportedly hated wearing it. This might come as a shock, as the costume appears to be one of the more comfortable on our list, but as Thurman told reporters when she first put it on back in 2003, she had just given birth to her son and didn’t yet feel comfortable in her new skin.
The form-fitting tracksuit revealed more than she was comfortable with, and she felt quite anxious about having to wear it (and move so actively in it) for months, day after day.
Audrey Hepburn’s transformative black-and-white gown
Audrey Hepburn and cast in a scene from ‘My Fair Lady.’
Salvador Perez, the president of the Costume Designers Guild from 2013 to 2022, once told The Hollywood Reporter the most iconic costume from the beautifully fashioned 1964 film “My Fair Lady” was Audrey Hepburn’s black-and-white ascot race dress and hat. The longsleeved lace dress, accessorized with graphic black-and-white ribbons and an elaborate hat sure made an impression even with several designers.
The ensemble inspired a good portion of Ralph Lauren’s Spring/Summer 2008 collection, and L’Wren Scott designed a red carpet outfit for Nicole Kidman in 2012 that was nearly identical to the original.
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Elizabeth Taylor’s gold, phoenix-inspired design
Elizabeth Taylor in a scene from ‘Cleopatra.’
Elizabeth Taylor wore over 65 costumes in “Cleopatra,” the film that would spark her infamous affair with Richard Burton and make her the highest-paid woman in the world. But the one that stands out the most is, without a doubt, her gold, phoenix-inspired getup. The bird on the cape is made of 24-karat gold and decorated with thousands of beads. Taylor’s outfits cost the film $194,800 on costumes (the largest budget for a single actor’s wardrobe in film history). It was auctioned off for a whopping $59,365 in 2012.
Twentieth Century Fox
Marilyn Monroe’s hot pink gown
Marilyn Monroe in a scene from ‘Gentlemen Prefer Blondes.’
The hot pink dress Marilyn Monroe wears while singing “Diamonds Are a Girl’s Best Friend” in “Gentlemen Prefer Blondes” was costume designer William Travilla’s backup option. He originally wanted to put the bombshell in a skin-toned bodystocking covered with fishnet hose and carefully placed jewels, but when her nude calendar scandal broke, producers insisted he return to the drawing board. So he came up with a pink silk dress lined with green billiard felt (for shaping) that she would essentially be folded and sewn into. His last-minute vision was clearly successful, and in 2010, the dress (or at least, one version of the dress) was sold at auction for over $300,000.
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Rita Hayworth’s strapless black satin gown
Rita Hayworth singing in the film ‘Gilda.’
Jean Louis, the mastermind behind the strapless black dress Rita Hayworth wears in “Gilda,” teamed up with the actress on nine other films. As a result of their longtime collaboration, he knew what would work on her body almost as well as she did, which allowed this moment of movie magic to take place.
The gown, worn during Hayworth’s striptease scene, is reportedly based on the dress in John Singer Sargent’s famous “Madame X” portrait and has three hidden stays in the torso that ensured it wouldn’t budge an inch no matter how risqué her dance moves got. The dress has come up for auction several times, but a sale has never been finalized, and the gown remains in a private collection as of this writing.
Keira Knightley’s emerald green gown
Keira Knightley and James McAvoy in a scene from ‘Atonement.’
Jacqueline Durran, the Oscar-winning costume designer who crafted the brilliant, emerald green gown Keira Knightley’s character wore in “Atonement,” told Entertainment Weekly the idea for the gown began with just two specifics from director Joe Wright: bare-backed and full-skirted.
A compilation of stylistic elements from the ’30s, ’40s, and early 2000s, the dress, worn in the film’s climactic scene, is an outfit that has really stuck with viewers thanks to its eye-catching color and sexy, sultry feel. Duplicates of the gown (some from the set, some made by outside parties) have sold for tens of thousands of dollars.
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