In the 30 years since the release of her debut album we’ve seen Madonna go from virgin territory to Earth mother and beyond.
But what’s the The Queen of Pop™’s all-time greatest fashion phase? EW’s style team sorted through all the rubber braceletes and girl-gone-bad torn lace, the cone bras and the crucifixes and finally managed to narrow down the list to seven of Madonna’s most iconic looks.
Dressed in a white wedding gown and veil, Madonna caused a stir at the 1984 MTV Video Music Awards with her performance of “Like A Virgin,” which kicked off with the singer perched atop a wedding cake and ended with her rolling around on stage. In 2012, Madonna admitted that her provocative writhing was actually an attempt to retrieve her stiletto. “I thought, ‘Oh my God; how am I going to get that? It’s over there and I’m on TV.’ So I thought, ‘Well, I’ll pretend I meant to do this,’ and I dove onto the floor. And I rolled around and I reached for the shoe, and as I reached for the shoe, the dress went up, and then the underpants were showing. And I didn’t mean to,” she explained.
Blondes may have more fun, but a brunette Madonna proved she could stir up plenty of trouble. With her hair dyed a darker shade, the singer paired her little black dress with a crucifix in the incendiary video for the 1989 single “Like A Prayer.”
Later that year, the pop chameleon went back to blond and dabbled in cross-dressing in the David Fincher-directed video for “Express Yourself.” The menswear inspired suit was cool, but what was with the monocle?
Madonna called her 1990 Blond Ambition Tour “musical theater,” Rolling Stone called it a “sexually provocative extravaganza,” and the Pope called for a boycott. The show went on, and the world was introduced to fashion designer Jean Paul Gaultier’s cone bra.
Madonna looked to the Far East to find outfit inspiration — a Gaultier kimono, thank you very much — for her performance of “Nothing Really Matters” at the Grammy Awards in 1999. “The whole idea of Geisha is a great metaphor for being an entertainer because on the one hand you’re privileged but on the other hand you’re a prisoner,” she told Entertainment Tonight. “I always have to get comfortable in front of the camera and get comfortable dancing on twelve-inch platforms.”
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