Fun fact: This Marie Antoinette-inspired costume Madge donned for her performance of “Vogue” at the 1990 MTV VMAs would later be worn by Glenn Close in the 1998 film Dangerous Liaisons.
8. Marilyn Monroe
Okay, so maybe this isn’t Madonna herself being iconic—rather, she’s aping a different iconic woman—but we have to admit that she does a pretty good Marilyn impersonation. She wore then in 1991 when she accompanied Michael Jackson to the 63rd annual Academy Awards after-party at Spago’s.
9. Sex (The Book, Not the Act Itself)
…We’re going to file Madonna’s book premiere look for her 1992 erotica tome, Sex, under “questionable.”
Up next: Madonna’s style goes to India, Japan, and more!