Madonna’s Most Memorable Outfits

Throughout her nearly four-decade-long career, Madonna has worn some very bold outfits. From three-piece suits to lingerie as outerwear, the Material Girl’s fashion choices are certainly never boring. Here are some of Madonna‘s most iconic looks.

A Look Inspired By North Africa

Madonna’s outfits for the MTV Music Video Awards never disappoint, and her 2018 look was no exception. The singer went for a North African-inspired look with an intricate headdress and layers of jewelry. However, some people accused her of cultural appropriation.

A Heavenly Look For The Met Gala

Madonna was very on-theme for the 2018 Metropolitan Museum of Art’s “Heavenly Bodies: Fashion & The Catholic Imagination Costume Institute” gala. Walking the red carpet with designer Jean Paul Gaultier, she wore a custom look that he created. It featured a black netted veil, a stunning crown composed of crucifixes, and numerous rosaries.

A Camo Gown

For the 2017 Metropolitan Museum of Art’s “Rei Kawakubo / Comme des Garçons: Art of the In-Between” Costume Institute gala, Madonna donned a military-inspired Moschino gown. She paired the dress with chain metal necklaces, black leather gloves, and a gold tooth. She was accompanied by Moschino designer Jeremy Scott.

A Suit With A Special Message

Honored as the “Woman of the Year,” the singer stepped out at the Billboard Women In Music 2016 event in a custom Gucci suit. Not only did the outfit feature floral and animal prints, but it also reportedly contained a secret message, according to Italian designer Alessandro Michele.

“[The suit was] made more special with embroidery that means ‘the Greek goddess of music that brings joy,'” he told Vogue.

Pretty In Purple

At the 2016 Billboard Music Awards, Madonna paid tribute to the late singer Prince in a “Purple Rain”-inspired three-piece lace suit like the ones that Prince wore in the 1980s. The outfit was again created by Gucci designer Alessandro Michele. Michele described Madonna’s tribute as a “real act of love” to Vogue.

A Matador Look For The Grammys

The Hollywood Reporter described Madonna’s outfit for the 2015 Grammy Awards as a “sparkly bullfighter-inspired bodysuit.” The Givenchy-designed look also featured a birdcage veil, fishnet tights and above-the-knee black leather boots. Not everyone was a fan, however, with some critics claiming she showed too much skin.

In Memory Of Tupac

Madonna showed off her love for the late singer Tupac Shakur (they dated once upon a time) with a graphic T-shirt at a Las Vegas after-party in 2015. Wearing her hair in long, tight waves, she completed the look with black leggings, gloves and a matching sweater tied around her waist. She also took the opportunity to accessorize with a super-shiny belt buckle and platform shoes.

Matching With Her Son

Madonna’s date to the 2014 Grammy Awards was none other than her son, David. The two wore coordinating tuxedos and hats. (Madonna’s was from Ralph Lauren.)

Boy Scout Chic

Never one to shy away from making a political statement, Madonna showed up in a Boy Scout costume to the 2013 GLAAD Awards. The outfit was considered a statement against the Boy Scout’s ban on openly gay members. “I think they should change their stupid rules, don’t you?” the singer said during the ceremony.

Feathers And All

Madonna dressed to impress at the 2013 Billboard Music Awards. She was decked out in a Givenchy look consisting of a feather jacket, a see-through fishnet slip and visible garters. Onstage, she also wore sunglasses.

A Vintage Movie Star Look

At a 2013 screening of “Madonna: The MDNA Tour,” the singer made a dramatic entrance. Wearing a black tuxedo and white waistcoat, some compared her look to that of actress Marlene Deitrich. Others thought her ensemble looked like a couture circus ringmaster costume.

A Super Outfit For The Super Bowl

As the headliner for the 2012 Super Bowl, Madonna didn’t just wow fans with her singing and dancing. She also made multiple costume changes during the show, including this gladiator look designed by Givenchy. All of her other outfit changes were designed by the French fashion house as well.

A Winning Look

This Reem Acra gown for the 2012 Golden Globe Awards landed Madonna on several “Best Dressed” lists. She made the look edgier with black fingerless gloves and a crucifix necklace. She won the award for “Best Original Song” for her tune “Masterpiece” in the movie “W.E.”

Little Red Riding Hood

Madonna looked like a grown-up Little Red Riding Hood at the 2011 premiere of “W.E.” in London. She wore fingerless leather gloves in a bright red hue and a long black Dolce & Gabbana cape over a Jean Paul Gaultier dress. She matched her vivid red lipstick to the gloves.

A Butterfly Dress

For the premiere of “W.E.” at the Venice Film Festival in 2011, Madonna wore a gown by Italian designer Vionnet. The otherwise basic gray dress was adorned with dozens of red butterflies. She paired it with oversized red sunglasses.

Showing A Lot Of Skin In London

During her Sticky & Sweet tour in 2008, Madonna performed in London wearing this revealing costume. The outfit included a see-through mesh leotard, black knee-high boots and a white top hat. Madonna’s signature fingerless black gloves also made an appearance.

Biker Chic

Madonna looked like a 1970s biker lady, decked out in purple at the 2005 MTV European Music Awards. She wore a purple-hued leather jacket and matching knee-high boots over a leotard. She completed the look with oversized sunglasses and Farah Fawcett hair.

A Cowgirl Look

In a Western-inspired look, Madonna wore a red suit to the 2000 Europe MTV Video Music Awards. The cowgirl ensemble was made more glam with rhinestone embellishments and a low belly-baring cut.

A Crimson Kimono

At the 1999 Grammy Awards, Madonna donned a bright red kimono to perform “Nothing Really Matters.” She wore the same look for the song’s music video. The kimono was designed by Jean Paul Gaultier.

Channeling ‘Beauty And The Beast’

For the 1998 VH1 Fashion Awards, Madonna chose a yellow gown that looked like a costume from the stage production of “Beauty and the Beast.” She won the “Most Fashionable Artist” award. Her dress was by designer Olivier Theyskens.

A Sublime Sari

The yellow gown was not the only outfit Madonna wore to the 1998 VH1 Vogue Fashion Awards. She also wore a blue sari. A sari is a traditional outfit worn by women in India.

Fire And Ice

In 1998, Madonna made a bold statement in a long, black cutout gown and pin-straight hair at the Fire and Ice Ball in Los Angeles. The event was a fundraiser to support the Revlon/UCLA Women’s Cancer Research Program. Perhaps that’s why she chose to go sans bra underneath the gown.

An Eastern-Inspired Look

Madonna showed off henna tattoos and distinctive Hindu facial markings at the 1998 MTV Video Music Awards. She was criticized by some Hindus for wearing the spiritual look while dancing provocatively onstage in the show’s opening number. Never one to shy away from controversy, Madonna released a statement that read, “The essence of purity and divinity is non-judgment. They should practice what they preach … If they’re so pure, why are they watching MTV?”

A Bustier Gown

Madonna wore a black bustier gown to pick up her “Best Actress” award for “Evita” at the 1997 Golden Globe Awards. She paired the cleavage-baring dress with long black gloves, and simple hair and makeup. The singer had given birth to her daughter Lourdes only a few months before.

1940s Madonna

In a red Givenchy dress, Madonna looked straight out of a scene in her 1996 film “Evita” at the movie’s Los Angeles premiere. The outfit evoked a 1940s feel. Madonna even struck an Eva Peron-like pose as she waved to the crowd.

A 1970s Look

Madonna, is that you? While on the road in 1993 for her “Girlie Show Tour,” the singer sported a big blond wig, belly-baring blue suede pants and a crop-top shirt with puffy sleeves. The whole look seemed straight out of the 1970s.

Sequin Lingerie

In 1993, Madonna performed in the U.K. as part of her Girlie Show tour. One of her costumes included a black sequin stage bra and shorts, long gloves and fishnet stockings. The ensemble was reportedly designed by Dolce & Gabbana.

Madonna As Marilyn Monroe

In 1991, Madonna attended the Academy Awards with none other than Michael Jackson. She dressed up in a Marilyn Monroe-inspired sequin gown. Her date wore sequins as well.

The Cone Bra

During a 1990 concert in Los Angeles, Madonna wore the cone-shaped bra that would later become one of her most iconic costume pieces. She wore a high ponytail and dramatic makeup to complete the look.

Looking Ultra-Glam

Madonna went for a glamorous look for the 1987 American Music Awards. She rocked light blond hair and a shimmery golden dress that nearly matched. Gold earrings and heavy makeup rounded out the look.


With short, peroxide-blond hair, Madonna took to the stage in 1987 wearing a corset decked out with gold tassels hanging from the nipples. She also used makeup to accentuate her eyes and lips, and applied a swipe of fiery red lipstick. The whole look was very burlesque-esque.

Bridal Garb

During a 1985 performance in Chicago, Madonna looked very bridal in an all-white ensemble. Notably, her cropped lace leggings were a major 1980s fashion trend, as was the crop-top jacket and bow headband. She wore her medium-length hair in loose curls.

Rocker Glam

At the 1985 American Music Awards, Madonna opted for a rocker glam look. She sported a black corset dress, motorcycle gloves and a bold red lip color. The crucifix necklaces she wore were also becoming part of her signature look.

Proud To Be A ‘Boy Toy’

For the very first MTV Video Music Awards in 1984, Madonna came dressed to make a statement. She wore white lace lingerie with matching gloves and a skirt and accessorized with strands of pearls and a belt buckle that proclaimed “Boy Toy.” She would perform her song “Like A Virgin” onstage in the all-white outfit.

A Kooky Look In London

In 1983, Madonna wore this colorful ensemble onstage while performing in London. Among the items attached to the pink ruffled skirt and corset were fake grapes and flowers, plastic red lobsters, and a baby doll. The singer completed the look with a coordinating hat and some flamboyant glasses.