2. 1988: Cher Turns Heads In An Unforgettable Sheer Dress
If there's one celeb who can be counted on for consistently show-stopping fashion, it's Cher. The singer and entertainer did not disappoint at the 1988 Academy Awards, turning heads on the red carpet in an incredible sheer Bob Mackie gown. Remember, this was before sheer red carpet gowns were trendy! At the time, the spiderweb-inspired dress was more than a little scandalous.