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.
1984
Ushering in a new decade of “more is more” attitude, she helped the excessive bracelets and legging layering trends thrive.
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.
1985
Wearing a cross-embellished white crop top and matching cross jewelry during a performance.
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.
1987
On her ‘Who’s That Girl?’ tour in gold and black nipple tassels by Jean Paul Gaultier.
1989
In her controversial “Like A Prayer” music video, Madonna danced around burning crosses wearing a cross necklace and black lacy slip dress.
1990
On her “Blonde Ambition” tour, Madonna unveiled the now iconic cone bra by Jean Paul Gaultier, instantly shocking everyone.
1990
On the “Blonde Ambition” tour in a beaded bra and headpiece.
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.
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.
1991
She turned heads while channeling Marilyn Monroe in a glam look at the 1991 Oscars with Michael Jackson in tow.
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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1998
Debuting yet another new era and look, Madonna showed up the 1998 VH1 awards in a blue sari, sparking some controversy.
1999
In a red Jean Paul Gaultier kimono during her performance of “Nothing Really Matters” at the 1999 Grammy Awards.
2001
When we thought she was embracing her new maternal side and then she turned around…
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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2012
For her ‘MDNA’ World Tour, Madonna freed the nipple in a see-through lace bralette while stripping during an on-stage performance.
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.
2015
At the 2015 Grammys, Madonna hit the red carpet in a cheeky Givenchy look baring it all in a black thong and fishnets.
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.
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.
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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.
From Harper’s Bazaar US
