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Hollywood's Most Daring Vintage Fashion Moments

1. Cher's Oscar Mohawk
It appeared that Cher was the originator of "the naked dress" on the red carpet, and her barely-there Bob Mackie gown at the 1988 Oscars overshadowed her Best Actress win that year for her role in Moonstruck. She beat Meryl Streep that night!

While people were buzzing over the Mackie creation — in both positive and negative ways — Cher didn't understand what the fuss was about. "Bob and I thought about [this dress] for a while. It went through so many changes. People were so weirded out about this dress, but I think it's quite appropriate for the evening," she told reporters backstage. 

While today we see the sheer gown as an iconic moment in Oscar red carpet history, it took a lot of guts to wear it. “We look back now and those designs seem amazing and fantastic, but it’s important to remember that the moment Cher stepped out of the limousine and into the spotlight, it wasn’t instantly known that what she was going to wear was going to be acceptable and not laughed at," FIDM curator Kevin Jones once said.

It took a lot of courage for the actress to stick to her aesthetic and ignore the Academy's warnings, and it all paid off in the end.