In the 30-plus years since the release of her debut album, we’ve seen Madonna go from virgin territory to Earth mother and beyond.
Sartorially speaking, that is.
But what’s the Material Girl’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.
Check out our picks below, then head down to the comments section to tell us which one gets your vote. Did we leave your favorite Madonna style moment out? Tell us why we are fools for not including her Desperately Seeking Susan phase, the dominatrix duds from her Erotica days, or Music‘s rhinestone cowgirl.
Like a Virgin
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.
In the music video for 1985’s “Material Girl,” Madonna paid homage to Marilyn Monroe in Diamonds Are a Girl’s Best Friend by wearing a pink stain dress, matching gloves and lots of bling. “I don’t think I’m like Marilyn Monroe in a lot of ways. The main thing that we have in common is that we bleach our hair,” she later told Smash Hits magazine.
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.
A new baby (daughter Lourdes) and a new religion (Kabbalah), had Madonna going back to basics. In the 1998 video for “Ray of Light,” the singer created a softer image with her denim jacket, natural curls, and red string bracelet.
Madonna looked to the Far East to find outfit inspiration — a Gaultier kimono, thank you very much — for her “Nothing Really Matters” music video in 1999; she echoed the style for her performance of the song at the Grammy Awards that same year. “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.”