Since she first hit the scene in the ’80s, you could always count on Madonna to get people talking (or gasping) about her look. Whether it be the controversial use of crosses, cone bras, or unapologetically sexy looks, the Queen of Pop has mastered the art of shocking people through fashion. Take a look back at some of Madonna’s most boundary-breaking outfit choices of all time.

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.

Madonna At MTV Awads

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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.

Madonna In New York

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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.

Madonna

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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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Photograph, Beauty, Photography, Arm, Shoulder, Long hair, Portrait, Hand, Chest, Black hair,

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.

Clothing, Fashion, Joint, Tights, Event, Costume, Footwear, Fashion model, Dress, Leg,

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1994

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

Madonna On Stage

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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.

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1995

For her MTV special promoting her sixth album, Bedtime Stories, Madonna exposed a leopard robe to reveal a sheer silk nightgown underneath.

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1996

At the premiere of Evita, Madge wore a red velvet dress decorated in roses.

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1998

Debuting yet another new era and look, Madonna showed up the 1998 VH1 awards in a blue sari, sparking some controversy.

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1998

In a very un-Madonna esque look, the singer attended the VH1 Awards in a yellow satin ball gown, looking like a gothic Disney princess.

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1998

In a leather and fur trimmed Versace gown at the annual Fire and Ice ball.

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1999

In a red Jean Paul Gaultier kimono during her performance of “Nothing Really Matters” at the 1999 Grammy Awards.

Red, Performance, Human body, Outerwear, Leg, Performance art, Stage, Event, Acting, Performing arts,

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2001

When we thought she was embracing her new maternal side and then she turned around…

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2001

The newlywed showed off her new last name in a white “Mrs. Ritchie” suit on the red carpet with husband Guy Ritchie.

Fashion, Fun, Event, Arm, Shoulder, Interaction, Outerwear, Gesture, Formal wear, Long hair,

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2005

Donning her headline-making “Hung Up” music video look, Madonna performed at the weekly G-A-Y night at The Astoria in London.

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2010

Going for a more elegant bombshell look, Madonna stunned at the Oscars after party in 2010.

2007 Vanity Fair Oscar Party Hosted by Graydon Carter - Arrivals

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2012

For her ‘MDNA’ World Tour, Madonna freed the nipple in a see-through lace bralette while stripping during an on-stage performance.

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2012

…And then she later took her pants off on-stage too.

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2012

For her Super Bowl Halftime Show performance, Madonna donned gold gladiator-inspired pieces while sitting atop a giant gold throne.

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2013

The singer went pants-free at the 2013 Billboard Awards, opting for a garter belt instead.

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2015

At the 2015 Grammys, Madonna hit the red carpet in a cheeky Givenchy look baring it all in a black thong and fishnets.

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2015

Going for a subtle naked dress look, Madonna wore a sheer chainmail dress exposing her black lingerie underneath at the iHeart Radio Music Awards.

Clothing, Dress, Fashion, Footwear, Blond, Carpet, Flooring, Costume, Fashion design, Style,

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2016

At the 2016 Met Gala, the Queen of Pop defended her see-through Givenchy look against ageist critics, saying she’ll continue to express her sexuality regardless of her age.

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2018

For the Heavenly Bodies: Fashion and the Catholic Imagination theme, Madonna donned a cross headpiece and black gown featuring a giant sheer cross over her chest.

Clothing, Red, Fashion, Dress, Victorian fashion, Costume, Costume design, Gothic fashion, Gown, Outerwear,

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2019

Debuting her Madame X album and era, Madonna has embraced an X-embellished eyepatch—and a fitting crown to go with.

Fashion, Gothic fashion, Performance, Goth subculture, Fashion design, Costume,

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