Are you a movie enthusiast who also loves fashion? Some of the most memorable outfits in movie history are eternally tied to the Hollywood legends who wore them. These looks are so iconic that we instantly recognize the films they come from. From Audrey Hepburn’s elegant black dress and pearls and Dorothy’s famous red slippers to Cher Horowitz’s preppy yellow plaid from Clueless, these are some of the standout ensembles from classic films.
Let’s start with Audrey Hepburn’s little black dress. “Breakfast at Tiffany’s,” released in 1961, is unforgettable for several reasons, though not all positive. Still, Hepburn’s dress has become timeless. Designed by Givenchy, this elegant representation of Parisian-inspired fashion was accessorized with opera gloves, sunglasses, a chunky pearl and diamond necklace, a tiara, and a croissant and coffee. It’s credited with launching the popularity of the LBD, or ‘little black dress,’ in the 1960s.
Next is Marilyn Monroe’s white dress. If you think of Marilyn Monroe, you might picture her in this iconic outfit. Sold at auction for $5.6 million in 2001, the halter neck cocktail dress was featured in the 1955 film “The Seven Year Itch” and was designed by William Travilla. The unforgettable scene where Monroe stands over a subway grate, with the air blowing up her dress, is fashion history. This dress is an iconic piece from the 1950s, a decade that celebrated knee-length dresses with full skirts, and Monroe herself was a fashion icon of that era.
Moving to the 1970s, Diane Keaton’s “Annie Hall” brought androgynous style into the spotlight in 1977. While the movie’s status may have shifted over the years, Keaton’s character sparked a new trend by swapping traditional female clothing for slacks, hats, and ties. Many of the costumes were Keaton’s own clothes and represented the ‘borrowed from men’ style. She later shared that her inspiration was the cool women of Soho at the time.
Then there’s Olivia Newton-John’s transformation in “Grease.” For the hit 1978 film, the actress wore a leather-look outfit so tight she had to be sewn into it. Accompanied by red mules and gravity-defying hair, this costume marked an abrupt shift in Sandy’s character. Created by Albert Wolsky, the pants, sewn from 30-year-old sharkskin, were a separate piece and so snug she could barely dance!
In 1961’s “West Side Story,” Rita Moreno stole the show. Her lilac dress during a dramatic dance sequence became iconic, even as the film set a benchmark for musical cinema. Irene Sharaff designed the outfit, and it accentuated Moreno’s Oscar-winning performance with its classic 1950s flair.
Fast forward to the ’90s, and one remarkable look from that era is Whitney Houston’s “Queen of the Night” outfit. Combining sci-fi and pop star fashion, her metallic bustier, chain skirt, thigh-high leather boots, and headpiece are unforgettable. Created by Susan Nininger, this costume was integral to the film’s story and recently fetched a significant sum at auction.
Lastly, there’s the unforgettable blue gingham dress worn by Judy Garland in “The Wizard of Oz.” This 1939 classic dazzled audiences with its vibrant Technicolor and remains beloved today. Dorothy’s blue dress, playful pigtails, and ruby slippers are iconic, inspiring countless Halloween costumes. The MGM wardrobe team crafted this legendary look, with a pair of the famous slippers housed at the National Museum of American History and another pair auctioned for roughly $6 million.
Which of these iconic retro movie looks is your favorite? For more style inspiration, why not explore the Lady Popular Fashion Arena?