Cybill Shepherd in 1985

Photo: © AP Photo/Liu Heung Shing

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Through the years, Cybill never shied away from making a statement. Here, she shows off the Day-Glo orange sneakers she wore to the 1985 Emmy Awards. "I remember when I walked in, half the women there hated me because I was comfortable," she says. "The other half of the women loved me because I knew next time they were coming to something like that, they were going to wear their tennis shoes."