9. 1954: Grace Kelly
Grace Kelly took dressing up for her first Oscar ceremony seriously. She came to the red carpet on Clark Gable’s arm and dressed in a timelessly elegant dress. For the event, Kelly wore a beaded organza ballgown with a ribbon-tied waist. She wore a string of pearls, a fur stole, and white elbow-length gloves.

That year, Kelly was nominated for her first Academy Award for Supporting Actress for her role in Mogambo, which she co-starred in with Gable. She was only 25 years old at the time. While Kelly lost to Donna Reed, she would go on to win her first and only Oscar the following year, for her role in The Country Girl.

While Kelly might have been disappointed to have lost the award, she still had a watershed year in ‘54. That was the year Alfred Hitchcock’s Rear Window premiered and shot her to the top of Hollywood’s A-list. In the next two years she would make six films, win an Academy Award, and fly off to Europe to marry the Prince of Monaco. 

While Kelly is synonymous with “style,” she wasn’t always interested in fashion. That all changed when she moved to New York to follow her acting career. Maree Frisby Rambo, Grace’s best friend from childhood, told Vanity Fair that Kelly wasn’t overly concerned with style when growing up in Philadelphia. “We all wore about the same thing. Sweaters and skirts and loafers and socks. It was like a uniform,” she said. But that changed when she came back from Manhattan to visit. “I remember she’d been in New York for a while. She came to Philadelphia, and I invited her to the Cricket Club to go swimming, and she appeared, and she just looked different. Whatever she had on was so chic, as opposed to us. She looked New York, where the rest of us looked Chestnut Hill.”