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Fashion Timeline: Madonna

Fashionism Timeline: Madonna

Christopher Turner

A look at Madonna, the ultimate fashion chameleon…

In a career over 26 years old that is showing no signs of stopping any time soon, Pop Diva Madonna has spent her entire career reinventing herself. She has consistently found a way to reinvent both her style of music and of fashion like no female artist has ever done before. The singer, actress and acclaimed author continues to prove that she is ahead of the times. By the time the world has caught on to the 'new' Madonna, she's already bored and ready to move on.

Here’s a look back at some of her most memorable looks:

Boy Toy Beginnings
April 1, 1985

Armfuls of rubber bracelets, crucifixes, torn t-shirts, tights, lacy bras and more were the unofficial uniform of New York's dance students through the late 70s. After signing her first singles deal with Sire Records in 1982, the budding pop star took the tattered look mainstream. As Madonna mania began in the early 80s, the advent of the "Madonna wannabe" began. As teenage girls around the country got the Desperately Seeking Susan look down pat, Madonna morphed into a new look.

Blonde Ambition
April 20th, 1990

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.

63rd Annual Academy Awards
March 25, 1991

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.

Viva Evita
December 14, 1996

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 Perón, 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.

70th Annual Academy Awards
March 23, 1998

Originally Madonna had planned an even more extreme Gaultier Goth gown, but she decided it was too over-the-top for the Academy Awards. On Oscar night she walked the red carpet in this 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
February 24, 1999

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 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
November 5, 2000

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 were courtesy of superstar Canadian designers Dsquared. This was also the beginning of the pop icon’s t-shirt statements. Here she declared her admiration for fellow pop-star Britney Spears.

Momma Madonna
June 7, 2005

Over the years Madonna’s style has evolved and matured. In 2005, she celebrated the release of her fifth children's book, Lotsa de Casha, in style with a kid-friendly event at Bergdorf Goodman in New York. The mother of two continued to show off a more sophisticated style with a stunning Dolce & Gabbana dress.

Confessions at the Disco
November 3, 2005

Madonna has transformed from pop icon to mother and back. The latest persona in her evolving image is that of a Disco queen. Only Madonna would dare revive Farrah Faccet’s 70s blonde flick hairdo and be able to pull it off. To mark her return to the dance floor the singer brings back her leotards and cut-off tights paying homage to the early disco days.

Vanity Fair Oscar Party
March 5, 2006

In 2006 Madonna arrived on the red carpet looking extra fabulous for the exclusive Vanity Fair Oscar after party. She ensured all eyes were on her in a dramatic pink Versace gown, revealing tons of cleavage. Of course vying for the limelight were those heavily muscled arms!

Another Year, Another Oscar Party
February 25, 2007

In 2007 Madonna returned to the red carpet for the 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.

I Am Because We Are
May 21, 2008

The pop diva wowed onlookers on the red carpet at the I Am Because We Are premiere at the 61st annual Cannes Film Festival wearing this stop-in-your-tracks belted, black and silver sequined Chanel Couture gown. It's shimmering, it's fringed, it's transparent. It may not be her best red carpet look but she still managed to prove she was the Queen of Cannes.