In the nearly 100 years that the Academy Awards have been in existence, the ceremony has become synonymous not just with film but fashion. Oscar dresses dominate the conversation the night of the festivities and for days after. They are praised when they are simply gorgeous and criticized when they miss the mark. Bold choices are applauded or mocked—or mocked at the time and then applauded later. (Looking at you, Björk.)
The anointing of the Oscars as a major event for clothes evolved over time as the ceremony went from being essentially a dinner party to a nationally televised event. In the early days, stars would rely on the studios to dress them, sometimes even working with the people who made their costumes on their films. Now the nominees and other attendees work with armies of stylists who connect them to high profile designers that are eager to have their work seen on as big of a stage as the Oscars red carpet.
Is there a dress code for the Academy Awards? These days that’s more unspoken. Still, in the past, there have been mandates for specific occasions. During the 1942 ceremony, held during World War II, the order was to dress modestly with “business suits and informal femme garb, obligatory.” Later, the famed costumer Edith Head was appointed the Oscars’ “fashion consultant.” In 1968, she announced that actresses “are requested to wear formal evening gowns either maxi or floor length,” among other suggestions so the women would not clash with the set. But still, her instructions were never really fully heeded, and the best dressers always took some risks.
With that said, here are some of the best red-carpet gowns ever to grace the Oscars.
Mary Pickford, designer unknown, 1930
One of the very first examples of a star bringing high glamor to the Oscars was when Mary Pickford, a star of silent films, won for Coquette, her first role in the talkies. She wore a beaded gown described as “Fragonard blue” that may have been the work of Jeanne Lanvin.
Audrey Hepburn, Givenchy, 1954
These days, Oscars fashion is all about designer collaborations, but when Audrey Hepburn took home her Academy Award for best actress, thanks to her charming work in Roman Holiday, that was not the case. She was an early pioneer, wearing what many have deemed a Givenchy dress with a boat neck, showing off her famous collarbone. But was it actually Givenchy? That, curiously, is up for debate. Kerry Taylor, who was responsible for selling the dress at auction in 2011, told me for my book Beyond the Best Dressed that it was actually designed by famed costume designer Edith Head for the film itself and then reshaped for the Oscar ceremony. Regardless, it remains one of the most perfect combinations of star and outfit in Oscars history.