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Fun Trivia Leslie Knope wore Buttercups riding costume in the 2013 Parks and Recreation episode, Recall Vote. Honorable Mention: The Woman in Red from The Matrix (1999) The Matrix (1999) Designer: Kym Barrett While she herself is not a character in 1999s The Matrix but rather a training distraction for Neo, her 1940s inspired bright red dress is certainly gorgeous, iconic, and very memorable

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Weve gathered outfits that stretch from the 1920s through the 2010s, giving you plenty of ways to dress up, look back and keep the conversation going across generations