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21. 1962: Rita Moreno
When Rita Morena won Best Supporting Actress in 1962 for her role in West Side Story, all eyes were on her fabulous dress. Her Japanese-influenced gown was so amazing, in fact, that she decided to wear it again to the Academy Awards 56 years later, in 2018!

When she took it out of her wardrobe, she was surprised it was still in pristine condition. “I would think it would tarnish! It’s been hanging in my closet,” Moreno, then 86, told Ryan Seacrest at the red carpet. She also wore the same elbow-length gloves that she did in '62. 

The dress was originally made in Manila in the Philippines, and the skirt was made from a single piece of obi fabric, which is traditionally used to create kimonos. "The fabric is obi, which is the what Japanese women use on their kimonos folded over and over,” she said.

While Moreno didn't reveal who designed the dress, her daughter gave more insight to Los Angeles Times, saying, “She bought the fabric herself and had an architect make it." So it could very well have been self-designed. This time around, Moreno also had the dress slightly updated to have it feel more modern, trading in the boat neckline for a strapless bodice design.