The Silver Screen‘s 25 Most Iconic Dresses

By: Mark Smith | Last updated: Sep 21, 2023

There is no way to overestimate the importance of costumes in the film industry. When done right, costuming can define not only the time and place, but also a character’s inner world, creating memorable moments that stand out for all the right reasons. In this article, we celebrate 25 of the most iconic outfits in film history, from classic Hollywood to modern blockbusters.

Audrey Hepburn Redefined Elegance

When Holly Golightly appeared in the very first scene of “Breakfast at Tiffany’s” everyone’s heart skipped a beat.

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Designed by Hubert de Givenchy, this iconic dress embodies chic and delicate 1960s fashion, and inspired generations of future fashionistas.

Grace Kelly Was a White Swan

Considered by director Alfred Hitchcock to be the epitome of the “Icy Blode” beauty, there’s no wonder her look in  In “To Catch a Thief” became so famous.

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 Grace Kelly’s white, strapless organza dress epitomizes elegance and sophistication.

Marilyn Monroe Became a Symbol

There are few images that are as synonymous with Hollywood magic as that of Marilyn Monroe, standing over a subway grate with her billowing white skirt.

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William Travilla’s cocktail dress, worn by Monroe in “The Seven Year Itch,” is an unforgettable moment in cinema history, although it did send Marylin’s then-husband into a rage.

Sharon Stone Was a Dangerous Woman

Sharon Stone’s portrayal of Catherine Tramell in “Basic Instinct” is accentuated by her bold and daring white, high-necked, sleeveless dress.

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Source: People.com

Designed to embody the essence of the character, this costume adds depth to the film’s groundbreaking portrayal of sexuality.

Olivia Newton-John's Complete Overhaul

When we first meet Olivia Newton-John’s Sandy, her innocence is highlighted by her cute, girlish outfits. But by the end of the movie, when she emerges with high-waisted black spandex pants, we know that she’s a changed woman.

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 This 1950s fashion classic was apparently so tight that it needed to be sewn onto poor Olivia.

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Reese Witherspoon's Color in the Courtroom

Reese Witherspoon’s Elle Woods brought brains, skills, and endless style to the court of law in “Legally Blonde”.

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The cult classic popularized pink as a signature color, with the pink look, highlighting the character’s vibrant and confident personality.

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Judy Garland's Technicolor Magic

Dorothy’s blue-and-white gingham dress in “The Wizard of Oz” became an iconic symbol of cinematic history.

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Rediscovered decades later, the dress displayed signs of frequent mending due to Garland reportedly ripping it several times during her portrayal of the character.

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Madonna's Eclectic New York Look

It’s not surprising to discover that in “Desperately Seeking Susan,” Madonna’s wardrobe was drawn from her own closet, since, according to the film’s director, she embodied the essence of 80s Manhattan.

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Her iconic fashion status is no secret to anyone that is familiar with her work.

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Alicia Silverstone Was the Queen Bee

Who other than Cher Horowitz can pull off a yellow plaid suit?

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Alicia Silverstone’s Dolce & Gabbana suit in “Clueless” became an emblem of 1990s fashion, symbolizing the film’s iconic style.

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Julia Roberts, a Lady in Red

Vivian Ward’s red gown in “Pretty Woman” exemplifies her transformation into a sophisticated lady, while still maintaining the character’s flair.

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The stunning costume, initially intended to be black, proved to be the perfect choice for Vivian’s character.

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Maggie Cheung's Cultural Heritage

In “In the Mood for Love,” Maggie Cheung’s character showcases 50 exquisite cheongsams, each one conveying her emotions throughout the film. The most memorable one, however, is her rose-covered one, which she wears during her confession.

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La Bella Donna: Anita Ekberg

The black strapless gown in “La Dolce Vita” was a breakthrough for Italian fashion.

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With its clean lines and flattering design, it reflects the era’s style of accentuating the figure and hugging every curve.

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Diana Ross' Orange Rebellion

Not only a world-class singer and actress, Diana Ross is also a fashion icon. Ross designed over 50 looks for her character in “Mahogany,” and sparked a change in the perception of flashy and brightly colored clothing.

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At the time, these were often thought of as cheap or tasteless.

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Vivien Leigh Doesn’t Give a Drape

The green “curtain” dress worn by Vivien Leigh as Scarlett O’Hara in “Gone with the Wind” has become a timeless piece of movie history.

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 It represents her resourcefulness and determination after her epic fall from grace.

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Sarah Jessica Parker’s Wayward Wedding

Carrie Bradshaw’s enormous Vivienne Westwood wedding gown in “Sex and the City: The Movie” captured the essence of Bradshaw’s larger-than-life sense of style and her enormous love of fashion, which are so synonymous with the character.

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Not to mention the bird she wore to accompany it.

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Lisa Kudrow and Mira Sorvino's Revenge Dress

In “Romy and Michele’s High School Reunion,” the pink and blue metallic minidresses worn by Kudrow and Sorvino stand out as a testament to their friendship.

Source: wmagazine.com

Apparently, Kudrow specifically asked that they showcase their bond with their outfits.

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Diane Keaton’s Quirky Ensembles

Annie Hall’s menswear-inspired outfit in Woody Allen’s “Annie Hall” sparked a trend in women’s fashion, celebrating bold and unconventional choices.

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Yet, rumors behind the scene state that the film’s costume designer wanted to overrule them all!

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Whitney Houston Was the Future

Inspired by the movie “Metropolis,” Whitney Houston’s futuristic performance costume in “The Bodyguard” is an absolute stunner.

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The piece was later auctioned off with the starting bid being $10,000!

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Kate Winslet Sailed in Style

“Titanic” had its fair share of amazing costuming, but Rose’s red-and-black sequined dress was a moment for the ages.

Source: stuff.co.nz

 It became a symbol of her transformation and the beginning of her star-crossed love story.

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Uma Thurman Was a Halloween Inspiration

Apparently, Uma Thurman really didn’t like this Bruce-Lee-inspired costume, despite its rather comfy look.

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The skintight black-and-yellow tracksuit in “Kill Bill” became a favorite Halloween costume but was initially uncomfortable for the actress, as she had just given birth.

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Audrey Hepburn's Ascot Ensemble

In her fabulous role as Eliza Doolittle in “My Fair Lady,” Hepburn’s black-and-white ascot dress would have floored the British aristocracy even today.

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It captured the essence of elegance, inspiring fashion designers and captivating audiences.

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Elizabeth Taylor, a Goddess in Gold

Elizabeth Taylor’s phoenix-inspired gown in “Cleopatra” is a breathtaking masterpiece of luxury and extravagance.

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The bird on its cape was reportedly made out of real, 24-karat gold, and costuming as a whole cost the film $194,800!

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Marilyn Monroe Shone Bright Like a Diamond

Apparently, Monroe’s iconic hot pink dress in “Gentlemen Prefer Blondes” wasn’t even the costume designer’s first choice!

Source: people.com

Originally, the costume designer planned a skin-colored outfit, but due to a nude calendar scandal, he improvised and created the pink silk dress.

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Rita Hayworth's Was More than Desent

Rita Hayworth’s now-legendary hair flip wasn’t the only memorable thing to come out of the movie “Gilda”.

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Her strapless black dress was a sophisticated piece, that was reportedly inspired by John Singer Sargent’s famous “Madame X” portrait!

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The Silky and Statuesqe Keira Knightley

Keira Knightley’s emerald green gown in “Atonement” combines elements from different eras, including the ’30s, ’40s, and early 2000s, to create a timeless and alluring piece that remains etched in viewers’ memories.

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Who could forget such an iconic piece?!

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