Maverick Style Files: The 10 Most Rebellious Dressers of All Time

Remember when Lady Gaga wore pieces of raw flank steak strung together at the 2010 MTV Video Music Awards? Or when Marlene Dietrich wore a tuxedo to play cabaret singer Amy Jolly in the 1930 film Morocco? Perhaps you can recall the jewelled “naked” gown Cher wore in 1988 to collect the gong for best actress at the Oscars? All three of these women have something in common: When it comes to fashion, they’re fearless (and unafraid to end up on worst dressed lists). To celebrate their most rebellious outfits, we’ve rounded up 10 shining examples for you to scroll through.

Christina Aguilera

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Christina Aguilera shook off her squeaky-clean Mickey Mouse Club image when she wore an itsy-bitsy bikini top with these skintight leather chaps back in 2002. It was also the year her album Stripped was released. She kept its name in mind when choosing her outfit for the album cover, as she wore bleached jeans and nothing else.

Rei Kawakubo

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The Japanese creative director of Comme des Garçons proves that even fashion mavericks can live in a uniform of sorts. Rei Kawakubo, who founded her iconoclastic label in 1969, studied art and literature at university instead of fashion design. She’s rarely seen out of head-to-toe black, hence the nickname given to her followers: “the crows.”

Marlene Dietrich

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No one bats an eyelid at a woman wearing a trouser suit today, but back in the ’30s, it was considered taboo. Marlene Dietrich wore hers with a top hat and bow tie to really hammer the message home in the 1930 film Morocco.

Lady Gaga

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Never has a single garment received quite as many column inches as Lady Gaga’s dress made out of raw cuts of flank steak. In an interview with Ellen DeGeneres (who happens to be vegan), Gaga said, “As you know, I am the most judgment-free human being on the earth. However, it has many interpretations but for me. … If we don’t stand up for what we believe in, and if we don’t fight for our rights, pretty soon we’re going to have as much rights as the meat on our bones.”

Michéle Lamy

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It seems like Michèle Lamy has squeezed five lives into her 74 years. She’s worked as a lawyer, a cabaret dancer, the owner of Les Deux Cafés (an L.A. spot where celebrities and socialites gathered in the ’90s) and a singer. As Rick Owens’s other half and a blazing creative in the art and fashion worlds, Michèle is recognised for her work as much as her look: She pencils her forehead with eyeliner, dips her fingers in Japanese vegetable dye to make them black, and wears gold and diamond grills. She’s easy to pick out of the sea of street stylers at Paris Fashion Week, that’s for sure.

Cher

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If you think today’s Instamodels invented the “naked” dress, think again. The year was 1974, and Cher wore an entirely sheer gown with white feathers trailing from sleeves and some strategically placed silver on the body to the Met Gala. In 1988, she cemented the trend in this barely-there Bob Mackie creation at the Oscars, where she won Best Actress for her role in Moonstruck.

Grace Jones

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The award for the most outrageous and on-point stage outfits goes to Grace Jones by a landslide. The 70-year-old has worn everything from a tiger-print bodystocking to a spangled Cleopatra-style headdress in a career spanning four decades. She also hasn’t lost her bite one bit, either.

Daphne Guinness

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Daphne Guinness’s blonde-and-black Cruella de Vil beehive is almost as famous as her shoes, which tend to be vertiginous platforms without any visible heel. The 50-year-old muse to Alexander McQueen and owner of the late Isabella Blow’s entire wardrobe told Vogue in 2005, “I like the really show-offy pieces; I always do!”

Coco Chanel

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We owe a lifelong debt of gratitude to Coco Chanel for making jersey and trousers not just acceptable but desirable. She also debuted her first tweed suit (a staple of Karl Lagerfeld’s present-day collections) as early as 1923—four decades before Yves Saint Laurent’s Le Smoking tuxedo.

Iris Apfel

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She has spectacles the size of saucers, enough necklaces to fill Aladdin’s cave and 96 years of inimitable stylishness under her belt. No rebellious dresser list would be complete without Iris Apfel, who told The Guardian earlier this year that she’d like to be remembered “as the world’s oldest living teenager.” Her everything-but-the-kitchen-sink fashion sense gets better with age.

Think of these ladies the next time you reach for a safe navy jumper and jeans.