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Hollywood's Most Daring Vintage Fashion Moments

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28. Kim Basinger's Mashup Dress
In 1990, Kim Basinger wore one of the most controversial gowns in red carpet history to the Oscars: her half-tuxedo, half-ballgown dress. Following the success of Batman and 9½ Weeks, Basinger was one of the most buzzed-about actresses that year. She was untouchable, and decided to mark the occasion with a custom dress she designed herself. The "Frankenstein-like ensemble" (Vogue's words) had one collar popped, one arm gloved, and one satin sleeve with musical notes. 

It was unusually wild, and some wondered whether her current beau inspired the look. "Some snide fashion wags were sure it was designed by Prince, her current squeeze," The Los Angeles Times wrote in 1990. Their relationship was so serious that Basinger gave up acting at the time and moved to Minneapolis to live with him.

“Prince is all half-and-half, though; male/female, Gemini — and I’m sure Kim thought it was a really great representation,” Helen Hiatt, Prince’s costume supervisor of the era, told The Hollywood Reporter. But Hiatt admitted that Prince's team wasn't the one behind the creation. "It was a surprise to all of us when we saw it; we did not make it for her." It was all Basinger's creation.