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10. 1955: Grace Kelly
Grace Kelly not only made headlines in 1955  because she won her first and only Academy Award, but also because she wore a news-worthy gown that was fit for a Hollywood starlet. The blue, French silk gown Kelly wore was designed by none other than the legendary costume designer Edith Head, who received 35 Oscar nominations and eight wins in her long career in the film industry. According to Elle, Head described the hue as "blue champagne," and it went on to become one of the most memorable gowns in Academy Awards history. 

At the time, it was considered to be the most expensive Oscars dress ever made, with the silk alone running $4,000. But apparently Kelly was able to get her cost-per-wear price lowered since the Oscars weren't the first place she wore the gown to. She also wore the mint column dress to the New York premiere of The Country Girl the year before!

When it came to trusting Head with creating her Oscar outfit, Kelly couldn't have chosen a better designer: Since the first year the Academy Awards were televised in 1953, Head was named the Oscars’ first fashion consultant. “I was appointed guardian of hemlines and bodices,” she said, tasked with the job of making sure starlets' dresses wouldn't scandalize the censors. 

"She was that backstage guardian at the ready with panels of lace and bunches of flowers to cover up décolletage until 1981," Los Angeles Timeswrote. By entrusting Head with her Academy Award outfit, Kelly knew she would not only be one of the most best dressed actors on the red carpet, but would also be above board with the censors.