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1984

For her first award show performance at the MTV VMA's, Madonna left a lasting impression with her white sheer "Like a Virgin" look. Complete with the now iconic "Boy Toy" belt, lace gloves, and cross necklaces, it kicked off her natch for creating buzzy looks.

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1984

Ushering in a new decade of "more is more" attitude, she helped the excessive bracelets and legging layering trends thrive.

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1985

During one of her first-ever concerts at Madison Square Garden, Madonna wore a sheer lace bra and matching leggings with a bundle of cross necklaces—a risk-taking look at the time.

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1985

Wearing a cross-embellished white crop top and matching cross jewelry during a performance.

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1987

In one of her more rarely-seen performance looks of the '80s, Madonna wore a red dress and hat adorned with hundreds of tiny items from dolls to plastic grapes and buttons.

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1987

On her 'Who's That Girl?' tour in gold and black nipple tassels by Jean Paul Gaultier.

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1989

In her controversial "Like A Prayer" music video, Madonna danced around burning crosses wearing a cross necklace and black lacy slip dress.

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1990

On her "Blonde Ambition" tour, Madonna unveiled the now iconic cone bra by Jean Paul Gaultier, instantly shocking everyone.

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1990

On the "Blonde Ambition" tour in a beaded bra and headpiece.

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1990

The Queen of Pop performed her hit "Vogue" at the 1990 MTV Awards dressed as Marie Antoinette. Keeping her performance anything but reserved, she made sure to flash her garter belts to the audience throughout the performance.

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1990

In a fur-trimmed corset dress on her "Blonde Ambition" tour.

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1990

Giving part I Dream of Jeanie and part Barbie vibes, one of her 'Blond Ambition' tour looks featured pink fur trim and bedazzled money signs.

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1991

For her Cannes Film Festival debut, Madonna walked all the way to the top of the red carpet stairs in a massive pink satin jacket which she then ripped off to unveil a cone bra and underwear. Iconic.

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1991

In a colorful sequin and jewel-encrusted bodysuit—sans pants—and a silk black robe with Alek Keshishian, the director of her Truth or Dare documentary.

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1991

She turned heads while channeling Marilyn Monroe in a glam look at the 1991 Oscars with Michael Jackson in tow.

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1991

For another outing with the King of Pop, Madonna stepped out in a black sheer naked dress and over-the-knee stockings.

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1992

For the release of her controversial book, SEX, Madonna went full-on milkmaid and carried a stuffed animal lamb, as one does.

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1994

In a beaded bra, shorts, and fishnets while performing at Madison Square Garden.

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1994

Making a runway appearance for Jean Paul Gaultier, Madonna hit the catwalk in a sheer, gold embellished gown while pushing a baby carriage.

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1994

The Queen of Pop wore a blue belly shirt and maxi skirt for a Los Angeles premire.

Lauren Alexis Fisher is the Senior Editor at Cosmopolitan, overseeing digital content across fashion, lifestyle, beauty, sex, and culture. Previously, she was the Market Editor at Harper’s BAZAAR and has written for publications including WWD, Bustle, and W Magazine. When she’s not busy taste-testing her way through every dirty martini in New York, you can follow her on Instagram for bad jokes, good outfits, and annoying vacation pics. 

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