From Diane Keaton’s wardrobe in Annie Hall to Marilyn Monroe’s famous white dress in The Seven Year Itch, check out the top ten most iconic looks in film history.
1. Annie Hall, Annie Hall (1977)
Diane Keaton, who starred in the 1977 films title role, sparked a fashion craze and revolutionized the menswear trend thanks to her characters unparalleled style. Annie Hall’s trademark high waisted trousers, white shirt, tailored waistcoat, flamboyant tie and bowler hat continue to influence androgynous fashion to this day. The characters style was based on Keaton’s own wardrobe, who supplied many of the items worn in the film from her own closet.
As one of the most defining films of the 1990’s, Clueless showcased and inspired some of the decade’s fashion trends. Cher Horowitz (Alicia Silverstone), the spoiled yet charming California blonde, was a self-proclaimed expert in “important” designers such as Fred Segal, Azzedine Alaia, and Calvin Klein. Cher’s signature school-girl style became iconic unto itself, her most memorable outfit was her yellow tartan plaid skirt and blazer set, complete with over the knee white socks.
3. Holly Golightly, Breakfast at Tiffany’s (1961)
Audrey Hepburn’s turn as Holly Golightly in the 1961 classic Breakfast at Tiffany’s cemented the actress’s place in fashion history. The most famous little black dress of all time, worn in the opening scene of the film, was designed by Hubert de Givenchy (founder of fashion house Givenchy) and paired with satin black elbow-length gloves, Oliver Goldsmith tortoiseshell sunglasses, and the unforgettable five-layered pearl necklace designed by french jeweler Roger Scemama.
Sandy’s (Olivia Newton-John) evolution from staid 1950’s full skirts, fitted sweaters and pom-poms to tough biker chic is one of the most memorable moments in the 1978 classic. Wearing black skin-tight leather pants (which Newton-John were famously sewn into on set), a black off-the-shoulder top, and red mules, Sandy’s transformation in the final scene of the film marked her spot in film fashion history.
Set against the backdrop of the picturesque French Riviera, To Catch a Thief remains Hitchcock’s most glamorous film. Frances Stevens’s (Grace Kelly) awe-inducing wardrobe is a hybrid of elegant and daring, and it is her ice blue chiffon evening gown that has become synonymous with the film itself. The floor length dress, with a fitted bodice and detailed with a knot draping onto the waist and skirt, was designed by legendary costume designer Edith Head, whose film credits include Sabrina, All About Eve and Rear Window.
6. Vivian Ward, Pretty Woman (1990)
Vivian Ward’s (Julia Roberts) transformation from prostitute to sophisticated lady of luxury is highlighted through her wardrobe. The phenomenal floor-sweeping red ball gown worn during the film’s opera scene marked Vivian’s complete evolution into elegance. The dress, with a daring v-cut and off the shoulder sleeves, was paired with elbow length white silk gloves and a sparkling diamond necklace.
Bond girl Honey Ryder (Ursula Andress) emerging from the ocean in a white bikini has long been considered an iconic moment in cinematic fashion history. The famous white bikini was designed by Andress along with the films costume designer Tessa Prendergast, with the bikini’s bottom detailed with a white British Army belt with brass knuckles, fittings, and scabbard meant to hold a large knife. Following the release of the film, sales of two-piece bikinis skyrocketed.
As Stanley Kowalski in 1951’s A Streetcar Named Desire, Hollywood bad boy Marlon Brando made t-shirts the must-have fashion item for men. Contrary to his elegantly dressed counterparts, Brando’s tight, sweaty t-shirt that placed his muscular torso on full display instantly equalled rugged-chic, and parlayed the benefits of wearing t-shirts in public to the forefront.
In the most famous scene from the 1946 film, Gilda (Rita Hayworth) performs the song “Put The Blame On Me” and improvises a striptease, but it is her black gown that stands out above all. The strapless black satin gown was created by renowned costume designer Jean Louis.
The infamous shot of Marilyn Monroe standing on a subway grate as the wind billowing from below blows up her white, pleated halter dress revealing her legs is easily one of films most iconic moments. The dress was created by Academy Award winning costume designer William Tavilla, and is a popular element of Monroe’s legacy. In 2011, the dress was sold at an auction for $4.6 million.