Top 5 Most Outrageous Madonna Outfits

  Madonna is no stranger to acting, and her performance in this biopic is one of her proudest moments– but her Evita-influenced fashion choices didn't end when filming wrapped. Gracing LA’s Shrine Auditorium in a sumptuous scarlet dress, an elaborate veiled hat, and Manolo Blahnik heels, it was as though Perón herself arrived for the occasion. The night didn’t go off without a hitch, however, as animal rights group PETA were on scene to protest the inclusion of a fur coat worn by Madge in the film. Still, reporters and fans adored her homage to the Argentinian First Lady. One month later, Madonna won the Golden Globe for Best Actress in a Musical or Comedy. No crying here!

As the saying goes, if you got it, flaunt it. Madonna did just that at the 2005 MTV Europe Music Awards in Lisbon. Days away from dropping her album Confessions on a Dance Floor, she kicked off the night with her hit single “Hung Up,” wearing a purple leather jacket, matching bodysuit, shades, and knee-high boots. Midway through her performance, Madge took off her jacket, revealing her killer curves and toned arms. Add in some suggestive dancing, and you’ve got yourself a showstopper. Madonna wasn’t nominated for any awards that night, but she definitely won over the crowd – at 47, no less! Over a decade later, she’s still giving us major fitness goals.

  Eva Perón wasn’t the only famous blonde Madonna has emulated. In the music video for her 80’s hit, “Material Girl,” Madonna struts around a set wearing a pink gown, just like one worn by Marilyn Monroe in “Gentlemen Prefer Blondes.” The red backdrop, tuxedo-clad dancers, and ever-present diamonds make this a pretty accurate tribute. Okay, the lanterns aren’t women, and there aren’t any flower girls, but close enough. Here, Madonna meant to show herself as an empowered woman, paving the way for her status as a style and music icon, albeit with a little help from Marilyn. Maybe diamonds are a girl’s best friend after all!

  The following year saw Madge trade blatant sex appeal for a mix of rebellion and religious iconography at the American Music Awards, but the 1984 VMA outfit was a hard one to follow.  Stepping down from a wedding cake wearing a white dress, matching fingerless gloves and veil, crosses, and the cheeky “boy toy” belt, Madonna proved she knew how to make an impression. The racy nature of her performance, outfit, and the song itself caused a lot of controversy, but this only boosted Madonna’s star power. Nineteen years later, fellow pop royalty Britney Spears and Christina Aguilera took on the look for a risqué tribute of their own at the 2003 VMAs. 

  The Queen of Pop has never been one to conform, and this outfit is a prime example. In 1990, Madonna introduced her pointy silk bustier during the Blond Ambition Tour. It was designed by French couturier Jean-Paul Gaultier, inspired by 1950’s bullet bras and the trend of wearing lingerie as clothes. The bustier eventually sold at auction in 2012 for $52,000 and continues to be a pop culture staple that has been referenced by the likes of Katy Perry, Glee, and even Weird Al Yankovic! Madonna herself revisited the look for her 2012 MDNA Tour, sporting a more deconstructed black bustier. The cone bra is not only among Madonna’s signature looks; it’s also a cultural phenomenon.  Do you agree with our list? What’s your favourite Madonna outfit? For more provocative Top 5s published daily, be sure to subscribe to MsMojo.