30 of Madonna's Most Groundbreaking Fashion Moments

Madonna during her Blond Ambition Tour in 1990. — Gie Knaeps / Getty Images

From a cone-shaped bra to a reimagined wedding dress, few pop culture icons have had as many memorable fashion moments as Madonna. The Queen of Pop has pushed music’s boundaries and has been equally impactful in terms of style. She has reinvented society’s notion of femininity by blending masculine elements into her looks on and off the stage, most notably through designs from Jean Paul Gaultier. In her early days, Madonna’s style can best be described with jelly bracelets, lace detailing, headbands, and everything else that made up the ‘80s.

Throughout her career, though, she has taken, sometimes controversial, fashion risks that have helped to pave the way for others to do the same. With the announcement of her tour, “Madonna: The Celebration,” kicking off in 2023, we thought we’d look back at the singer’s most avant-garde and memorable fashion moments throughout her career.

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MTV Video Music Awards (1984)

Madonna at the 1984 MTV Video Music Awards — Sonia Moskowitz / Getty Images

Who can forget this signature Madonna moment from the 1984 MTV Video Awards? True to her Like A Virgin-era, the singer wore a bridalcore lace look, complete with beaded rosary necklaces and a "boy toy" belt.

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On the Set of "Desperately Seeking Susan" (1985)

Madonna on the set of Desperately Seeking Susan in 1985

Madonna is best known as the Queen of Pop, but she’s also had some memorable silver screen moments throughout her career. For her role in Desperately Seeking Susan, Madonna perfectly captured the free-spirited fashion trends of the ‘80s, which didn’t stray far from her own style.

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Performing in Detroit (1985)

If you need 80s fashion inspiration, look no further than this picture of Madonna performing during her Virgin Tour in 1985. Everything from the lace tights to the multi-colored bomber jacket makes this look a signature of the decade.

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American Music Awards (1985)

Madonna at the American Music Awards in 1985

When it comes to Madonna’s accessories, more is more. For the 12th Annual American Music Awards, she wore a Jean Paul Gaultier corset top, naturally, and layers of rosary bead necklaces and netted gloves.

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"Desperately Seeking Susan" Premiere

Madonna at the 1985 premiere of Desperately Seeking Susan.

For the premiere of Desperately Seeking Susan, Madonna channeled her Like a Virgin outfit and wore a white gown with a white fur shawl and strands of pearl necklaces and rosaries.

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Filming "Papa Don't Preach" Video (1986)

Madonna filming "Papa Don't Preach" in 1986

We love a cheeky graphic tee moment, and apparently, so does Madonna. While on the set filming the music video for “Papa Don’t Preach,” the songstress kept it casual in an “Italian’s Do It Better” tee and trousers.

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American Music Awards (1987)

Madonna at the 1987 American Music Awards — Ron Galella / Ron Galella Collection via Getty Images

Madonna embraced old Hollywood for this Marilyn Monroe-esque look at the 1987 American Music Awards. That evening she took home the award for Favorite Female Pop/Rock Video.

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Blond Ambition Tour (1990)

Madonna performing during Blonde Ambition Tour in 1990. — Gie Knaeps / Getty Images

Madonna has had countless iconic fashion moments throughout her lengthy career, but perhaps the moment that solidified her place as a pop culture icon was when she kicked off her Blond Ambition Tour wearing a Jean Paul Gaultier cone bra corset.

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Blonde Ambition Tour (1990)

Madonna during Blonde Ambition tour in 1990.

The Blonde Ambition Tour had no shortage of stylish moments, like this hot pink and feather number the singer wore while performing in Tokyo, Japan.

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MTV Video Music Awards (1990)

Madonna at the 1990 VMAs. — Frank Micelotta/ImageDirect

Madonna has had her fair share of standout moments at the MTV Video Music Awards, including this performance where she embodied Marie Antoinette to sing “Vogue.”

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MTV Video Music Awards (1995)

Madonna at the 1995 VMAs — Kevin Mazur Archive / WireImage

In 1995, the singer took home the VMA for Best Female Video while wearing a silky blue blouse unbuttoned to expose a sheer black bra. While this is a fairly subdued fashion moment for Madonna, the look melds masculinity with femininity, which her style has become famous for.

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Golden Globes (1997)

Madonna kept things simple and sleek, wearing a black gown and black opera gloves to the 54th Annual Golden Globe Awards. That evening she took home the award for Best Actress in a Motion Picture Musical or Comedy for her role in Evita.

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VH1 Fashion Awards (1998)

Madonna at the VH1 Fashion Awards in 1998 — Frank Micelotta / Getty Images

At the 1998 VH1 Fashion Awards, Madonna accepted an award wearing a yellow corseted gown from Belgian designer Olivier Theyskens. Staying true to Madonna’s style, the long black hair and black accessories added a gothic element to this brightly colored look.

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Grammys (1999)

Posing with four Grammys may be the ultimate flex, but doing it in Gucci bedazzled pants and a white tank top is all the more iconic. Madonna wore this “cool-girl” look to the 1999 Grammy Awards, where she took home multiple awards, including Record of the Year and Best Pop Vocal Album.

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Europe MTV Video Music Awards (2000)

Madonna at the Europe MTV Video Music Awards in 2000 — Vinnie Zuffante / Getty Images

At the 2000 Europe MTV Video Music Awards, Madonna went cowboy-chic in a western-inspired red look with sparkling embellishments.

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MTV Video Music Awards (2003)

Madonna’s outfit may not be the most memorable part of her performance at the 2003 MTV Video Music Awards, but it didn’t disappoint. The singer wore an all-black fit with knee-high boots and a corset-style top.

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MTV Europe Music Awards (2005)

Madonna at the 2005 MTV Europe Music Awards

Powerful in purple. Madonna wore this retro-inspired ensemble to the 2005 MTV European Music Awards.

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Cannes Film Festival (2008)

Madonna at the Cannes Film Festival in 2008

Madonna sparkled in a Chanel couture gown at the premiere of I Am Because We Are at the Cannes Film Festival in 2008.

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Met Gala (2011)

Madonna graced the Met Gala steps in this sophisticated Stella McCartney gown at the 2011 Met Gala. The look is a step away from Madonna’s usual unconventional outfit choices.

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MDNA Tour (2012)

Madonna performing during MDNA Tour in 2012 — Kevin Mazur / WireImage

The infamous cone bra corset designed by Jean Paul Gaultier made its return during Madonna’s MDNA Tour in Hyde Park. This time, though, Madonna wears a cage-like version of the bustier top paired with pinstripe pants and a crisp white button-down.

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Met Gala (2013)

Madonna at the 2013 Met Gala — Dimitrios Kambouris / Getty Images

Madonna went back to her punk roots in a studded plaid blazer by Givenchy, along with thigh-high stockings and a black wig.

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Grammys (2014)

Madonna suited up for the 56th Grammy Awards in a black Ralph Lauren tuxedo, pairing the look with a bowler hat and a diamond-encrusted fingerless glove. The best part? Madonna brought her son, David, with her in a matching suit.

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Met Gala (2016)

Madonna looked stunning in Givenchy at the Manus x Machina: Fashion In An Age Of Technology Met Gala. She collaborated with Riccardo Tisci to create this sheer lace gown, styled with a body chain and a sparkling headpiece.

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Billboard Music Awards (2016)

Madonna at the 2016 Billboard Music Awards

Paying tribute to Prince, Madonna performed at the 2016 Billboard Music Awards wearing a custom Gucci metallic purple suit with paisley brocade detailing.

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Met Gala 2017

Madonna wore this camouflage Moschino gown to the 2017 Met Gala that’s fit for fashion combat. The gown was complete with a netted train and latex opera gloves.

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Met Gala (2018)

For the 2018 Met Gala, Madonna unsurprisingly enlisted Jean Paul Gaultier to create an ensemble inspired by the theme, Heavenly Bodies: Fashion & The Catholic Imagination. The result was a gothic black gown with a bejeweled headpiece and a black veil.

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Billboard Music Awards (2019)

Madonna at the 2019 Billboard Music Awards

Taking the stage at the 2019 Billboard Music Awards, Madonna wore a custom Erdem look to perform with Colombian singer, Maluma. The look consisted of a polka-dot dress, a black corset, fishnet tights, and an eyepatch worn to promote her latest project.

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