A Look Back At Madonna’s Most Iconic Fashion Moments

After more than four years, Madonna is back on the music scene with a brand new album — her first since 2015’s Rebel Heart. Madame X, which is officially out today, will serve as her 14th studio album.

Madame X is a concept album that has the undisputed Queen of pop taking on various different characters.

“Madame X is a secret agent. Traveling around the world. Changing identities. Fighting for freedom. Bringing light to dark places. She is a dancer. A professor. A head of state. A housekeeper. An equestrian. A prisoner. A student. A mother. A child. A teacher. A nun. A singer. A saint. A whore. The spy in the house of love. I’m Madame X.”

Of course, it’s not the first time Madonna has proved herself to be the ultimate chameleon. In a career spanning four decades, Madonna has spent her time in the spotlight consistently reinventing herself. In fact, she has found a way to reinvent both her style of music and of fashion like no female artist has ever done before. By the time the world has caught on to the ‘new’ Madonna, she’s already bored and ready to move on.

In celebration of the launch of Madame X… Here’s a look back at just a few of Madonna’s most memorable looks:

In the beginning…
Armfuls of rubber bracelets, crucifixes, torn t-shirts, tights, lacy bras and more were Madonna’s unofficial uniform while she was a dance student in New York during the late 70s. After signing her first record deal with Sire Records in 1982, and releasing her first single ‘Everybody’ later that year, the budding pop star took the tattered look mainstream.

“Like A Virgin”
Madonna made bridal wear chic in the early 1985, when she donned white lace, rosary beads and gloves for her “Like A Virgin” music video in 1984. The next year she pulled out the bridal look to open MTV’s very first Video Music Awards (broadcast on September 14, 1984) and for subsequent performances of the song on The Virgin Tour through 1985. Today her MTV Video Music Awards ensemble remains one of her most iconic looks… The wedding dress went on display at the Hard Rock Cafe in Times’ Square in 2011 and has spurred endless copycat Halloween costumes in the decades since.

Desperately Seeking Susan
As Madonna mania began in the early 80s, the advent of the “Madonna wannabe” began and Susan Seidelman’s 1985 film starring Rosanna Arquette and Madonna definitely contributed to the hype around Madonna’s look. But, as teenage girls around the globe got the Desperately Seeking Susan look down pat, Madonna morphed into a new look.

“Papa Don’t Preach”
In 1986, Madonna debuted a brand-new, understated “bad girl” look when she released the “Papa Don’t Preach” music video, the first single from her third album True Blue. Her cropped, peroxide-bleached hair and black biker jacket showed a different flavour of her edgy street style. Plus, how about that iconic “Italians Do It Better” t-shirt?

Blonde Ambition
In 1990, French designer Jean-Paul Gaultier designed the costumes for the Blond Ambition World Tour. Some consider Gaultier’s reinvention of underwear as outerwear in the design of Madonna’s iconic cone bustier which she flaunted onstage his most famous contribution to modern fashion. To this day it is Madonna’s most memorable look. Now “strike a pose”.

Channeling Marie Antoinette
For her performance of “Vogue” at the MTV Video Music Awards, which aired live on September 6, 1990, the Queen of Pop channeled original material girl Marie Antoinette. The stunning gown was originally made for the 1988 film Dangerous Liaisons, where it was worn by Glenn Close as the Marquise de Merteuil.

63rd Annual Academy Awards
For her 1991 Oscar appearance (performing the nominated song “Sooner or Later” from the film Dick Tracy) Madonna channeled Marilyn Monroe in a Bob Mackie beaded white strapless body-hugging dress complete with fur and formal length gloves. To top off her look, the ultimate fashionista was wearing $20 million worth of diamonds on her neck, ears, and wrists. “Sooner or Later” picked up the Oscar that night… and Madonna was a winner on the red carpet.

Truth Or Dare takes over Cannes
Madonna brought the cone bra back for the 1991 premiere of Truth or Dare (titled In Bed With Madonna outside North America) at the Cannes Film Festival in France. The cameras went wild when she dropped her pepto pink wrap and revealed another Jean Paul Gaultier conical bra, which was a pretty loose interpretation of the festival’s formal dress code.

Revitalizing Gucci
The fashion press loved the updated retro looks that replaced the minimalism of the early 1990s, but Gucci was struggling under Tom Ford who had recently taken over the heritage brand. It wasn’t until the brand earned an endorsement from Madonna (who wore the collection’s key look to the 1995 MTV Video Music Awards) that Gucci cemented the message that it was back…and all about glamour and sex. “Someone asked Madonna on camera what she was wearing [at the MTV Video Music Awards in 1995] and she said, ‘Gucci, Gucci, Gucci.’ That was really the beginning,” Tom Ford explained in his coffee table book published in 2008.

Viva Evita!
In 1996, Madonna’s most critically successful film, Evita, the movie adaptation of Andrew Lloyd Webber’s stage musical of the same name, was released. For years Madonna had petitioned to play the role of the life of Argentina’s Eva Peron, believing that this was the role she was born to play. After winning the coveted role she transformed herself into the equally controversial figure wearing glamorous Christian Dior suits complete with red lipstick and her hair bleached and pulled back into a knot. John Galliano created this opulent Eva Peron inspired look for the film’s premiere in Los Angeles.

70th Annual Academy Awards
Originally Madonna had planned an even more extreme Gaultier Goth gown, but she decided it was too over-the-top for the Academy Awards in 1998 and opted for a more “low-key” look. The Oscar presenter paired one of Jean Paul Gaultier’s elegant skirts with a black silk over-garment by a then newcomer named Olivier Theyskens. To be kind… Let’s just say the fashion press didn’t love it.

Memoirs of a Geisha at the Grammys
For one of those most over-the-top Grammy performances of all time, Madonna re-invented herself as a geisha, inspired by Arthur Golden’s book Memoirs of a Geisha. Madonna wanting to transform herself into one of the books characters, Hatsumomo wore a red kimono designed by Jean-Paul Gaultier, obscenely high platform boots and a jet black Cleopatra style wig for the 1999 Grammy performance. Considering very few artists can change their image on such a large scale, Madonna’s geisha-infused performance was a complete success.

Cowboy fever
Madonna released her album Music in 2000, returning to the charts and the fashion world with a cowboy-inspired incarnation. But this clean and simple country look wasn’t cheap. Her beaded jeans where curtsey of superstar Canadian designers Dsquared2. This was also the beginning of the pop icon’s t-shirt statements. Here she declared her admiration for fellow pop-star Britney Spears.

Mrs. Ritchie
Madonna made sure everyone knew she was Mrs. Guy Ritchie when she walked the red carpet at the Snatch premiere in 2001, wearing this bridal-white crystal-encrusted blazer. The couple tied the knot in December the previous year.

The Confessions era
To mark her return to the dance floor, and for her Confessions on a Dance Floor phase, Madonna favored Farrah Fawcett–style blonde hair and plenty of 70-inspired ensembles with leotards and cut-off tights paying homage to the early disco days.

Another year another Oscar party
In 2007 Madonna returned to the red carpet for the 79th annual Academy Award after party wearing a gorgeous strappy Dolce & Gabbana satin gown with a reported $10 million in diamonds from Neil Lane. The Vanity Fair after party is one of the most exclusive parties of the year and Madonna ensured she stunned in this black satin number.

The Louis Vuitton bunny ears
For “The Model as Muse: Embodying Fashion” Costume Institute Gala in 2009, Madonna donned this show-stopping Louis Vuitton ensemble, complete with bunny ears. It’s the same outfit she wore in the label’s much-hyped fall/winter ad campaign that year.

Couture punk
Dressed by former Givenchy creative director and Met Gala 2013 co-host Riccardo Tisci, Madonna ticked off the punk theme with as many metallic studs as the fashion house could feasibly fasten to one tartan blazer. Sans trousers and with a wisp of fishnet to preserve her modesty, the “Papa Don’t Preach” performer tapped into the spirit underlining the dresscode. “I wanted to do my own thing, but put my own twist on it,” she told reporters lining the red carpet, before referencing Sid Vicious, Nancy Spungen “and that whole era” as her influences.

Rebel Heart
Madonna unleashed her inner matador in 2015 as she began to promote her Rebel Heart album. When she walked the red carpet before hitting the stage to perform “Living For Love” at the at Grammys in LA she wore this heavily embellished custom-made Givenchy ensemble.

Madame X
Which leads us to Madonna’s latest reinvention. The Madame X era has only just begun, but so far we’ve been treated to plenty of sultry ensembles and bedazzled eye patches.

Tags: Academy Awards, Bob Mackie, Britney Spears, Christian Dior, Dolce & Gabbana, DSquared, DSquared2, Givenchy, Gucci, Jean Paul Gaultier, John Galliano, louis vuitton, madonna, Neil Lane, Olivier Theyskens, Tom Ford, top story, topstory

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