Madonna


Madonna wore Mackie at the 1991 Oscars where she performed Best Song winner “Sooner or Later” from “Dick Tracy.” If there had been an internet back then, she would’ve broken it, not just for the stunning Marilyn Monroe homage but also because she showed up with Michael Jackson as her date. Steven Meisel memorialized the instantly iconic look for the April ‘91 issue of Vanity Fair. (Oscar fashion nerds will be interested to know this was the only dress she wore that night. Compare to today where a celeb might have 2-3 outfit changes: one for red carpet arrival, one to present an award or perform, and one for the after parties.)

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