Cher in Bob Mackie, 1988

Cher at the 60th Academy Awards in April 1988, holding the Best Actress Oscar she won for Moonstruck. Two years after the feathered headdress, she and Bob Mackie went another way: a sheer gown traced with black beads and fringe, worn with a long beaded velvet stole. It was as daring as anything she had worn before, and winning the top acting prize in it made the point that an Oscar look could be outrageous and serious at the same time.