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gallery
July 13, 2015

See All of Madonna’s Most Iconic Looks

By Stephanie Eckardt

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Photo: Giovanni Canitano/REX/Copyright (c) 2006 Rex Features. No use without permission.

But Daddy, I’m having a good time, Madonna would plead with the man’s voice over the loudspeaker reprimanding her to come down from the stage. The recording played before she launched into “Material Girl” on each stop of the Virgin Tour in 1985, her first major tour in America. Though she’d only released two albums at that point, the singer had already amassed such a following that hundreds of fans showed up dressed so convincingly as her look-alikes that she could mingle in the crowd unnoticed before taking the stage.

In the three decades since, Madonna has sold over 300 million records and played hundreds of more shows, making her the top-selling female recording artist of all time and the so-called “Queen of Pop.” The Queen of Reinvention has been another well-earned moniker: Her image has seen plenty of overhauls in that time, too. There’s covered-in-rubber-bracelets Madonna, Marilyn Monroe Madonna, crucified Madonna, spiritual-kabbalist Madonna, and wearing-grills-with–Miley Cyrus Madonna. With all her incarnations, she’s wielded almost immeasurable influence on style across stages, runways, and movie sets around the world. (Could there even be a Lady Gaga if Madge’s fishnets, crucifixes, and cone bras hadn’t come first?)

Like a true devotee, Michelle Morgan mined through the queen of pop’s expansive career and created The Mammoth Book of Madonna: Celebrating 30 Years of the Queen of Pop, published by Running Press Books last month. Click through the slideshow to see some of the most noteworthy highlights, from her turns on the catwalk for Jean Paul Gaultier to the infamous onstage kiss at the Grammys in 2003.

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Wearing her graffiti tag, "Boy Toy," as publicity for her 1983 debut album, Madonna.  Photo: Michael Putland/1984 Getty Images
Playing a pregnant teenager in the controversial music video for "Papa Don't Preach." A couple of decades later, she wore a version of the s... Playing a pregnant teenager in the controversial music video for "Papa Don't Preach." A couple of decades later, she wore a version of the shirt that said "Kabbalists Do It Better." Photo: Vinnie Zuffante
Against a backdrop of burning crosses in the "Like a Prayer" music video, in which she also appeared with stigmata, causing Pepsi to drop th... Against a backdrop of burning crosses in the "Like a Prayer" music video, in which she also appeared with stigmata, causing Pepsi to drop their advertising deal. Photo: Phot Journalists/REX/Copyright (c) 1989 Rex Features. No use without permission.
Wearing the infamous Jean Paul Gaultier cone bra at London's Wembley Stadium on her 1990 Blond Ambition tour, for which Gaultier designed the costumes... Wearing the infamous Jean Paul Gaultier cone bra at London's Wembley Stadium on her 1990 Blond Ambition tour, for which Gaultier designed the costumes.  Photo: Eugene Adebari/REX/Copyright (c) 1990 Rex Features. No use without permission.
Dressed as Marie Antoinette while performing "Vogue" at the 1990 MTV awards.  Photo: Frank Micelotta
At the Cannes premiere of Truth or Dare, the 1991 documentary about her Blond Ambition tour. She appeared wrapped in a silk sheet and later dropped it... At the Cannes premiere of Truth or Dare, the 1991 documentary about her Blond Ambition tour. She appeared wrapped in a silk sheet and later dropped it to reveal her cone bra and underwear.  Photo: Sipa Press/REX/Copyright (c) 1991 Rex Features. No use without permission.
In a publicity still for her 1992 album Erotica, which was banned from MTV for being too risqué. Photo: Araldo di Crollalanza/REX/Copyright (... In a publicity still for her 1992 album Erotica, which was banned from MTV for being too risqué. Photo: Araldo di Crollalanza/REX/Copyright (c) 1993 Rex Features. No use without permission.
Pushing a puppy in an old-fashioned stroller down the runway for Jean Paul Gaultier in October 1994. Photo: STEVE WOOD/REX/Copyright (c) 1994 Rex Fe... Pushing a puppy in an old-fashioned stroller down the runway for Jean Paul Gaultier in October 1994. Photo: STEVE WOOD/REX/Copyright (c) 1994 Rex Features. No use without permission.
Performing "Bedtime Story," written by Björk, at the 1995 Brit Awards.  Photo: RICHARD YOUNG/REX/Copyright (c) 1995 Rex Fea... Performing "Bedtime Story," written by Björk, at the 1995 Brit Awards.  Photo: RICHARD YOUNG/REX/Copyright (c) 1995 Rex Features. No use without permission.
Posing with her four Grammy Awards in February 1999 after performing "Nothing Really Matters." Photo: CHARBONNEAU/BEI/REX/Copyright (c) 19... Posing with her four Grammy Awards in February 1999 after performing "Nothing Really Matters." Photo: CHARBONNEAU/BEI/REX/Copyright (c) 1999 Rex Features. No use without permission.
With Guy Ritchie in the couple's first official appearance together in February 2000, before marrying later that year.  Photo: RICHARD YOUNG/RE... With Guy Ritchie in the couple's first official appearance together in February 2000, before marrying later that year.  Photo: RICHARD YOUNG/REX/Copyright (c) 2000 Rex Features. No use without permission.
Wearing a tiara and dancing in front of a giant American flag with Rupert Everett in the 2000 video for "American Pie."  Photo: EUGEN... Wearing a tiara and dancing in front of a giant American flag with Rupert Everett in the 2000 video for "American Pie."  Photo: EUGENE ADEBARI/REX/Copyright (c) 2000 Rex Features. No use without permission.
Out in London in 2000, toward the end of her pregnancy with Rocco Ritchie. Photo: NIKOS/REX/Copyright (c) 2000 Rex Features. No use without permission.
Kissing Christina Aguilera and Britney Spears, who were dressed as brides, onstage at the 2003 MTV awards before introducing Missy Elliott.  Ph... Kissing Christina Aguilera and Britney Spears, who were dressed as brides, onstage at the 2003 MTV awards before introducing Missy Elliott.  Photo: Kevin Kane
Riding a horse for the first time since her accident, after telling David Letterman her record company wanted her to avoid riding until after her Conf... Riding a horse for the first time since her accident, after telling David Letterman her record company wanted her to avoid riding until after her Confessions on a Dance Floor album came out the next month in November 2005.  Photo: Charles Sykes/REX/Copyright (c) 2005 Rex Features. No use without permission.
Wearing a crown of thorns and mounted on a disco-themed cross singing "Live to Tell" on the controversial 2006 Confessions tour, after which... Wearing a crown of thorns and mounted on a disco-themed cross singing "Live to Tell" on the controversial 2006 Confessions tour, after which she released a statement asserting she was not mocking the church.  Photo: Giovanni Canitano/REX/Copyright (c) 2006 Rex Features. No use without permission.
Skipping rope onstage at the Madison Square Garden stop of Sticky & Sweet, her eventful 2009 tour during which she divorced Guy Ritchie, and a sta... Skipping rope onstage at the Madison Square Garden stop of Sticky & Sweet, her eventful 2009 tour during which she divorced Guy Ritchie, and a stage collapsed and killed two crew members.  Photo: REX/Copyright (c) 2008 Rex Features. No use without permission.
On the New York set of W.E., a film about the romance between Wallace Simpson and Edward Windsor that she wrote and directed, and later called "a... On the New York set of W.E., a film about the romance between Wallace Simpson and Edward Windsor that she wrote and directed, and later called "a bloody nightmare" because of its various shooting locations and time spans.  Photo: Greg Allen/REX/Copyright (c) 2010 Rex Features. No use without permission.
Matching Miley Cyrus in cowboy gear for an MTV Unplugged concert in January 2014, where they sang "Don't Tell Me" and "We Can't Stop.&q... Matching Miley Cyrus in cowboy gear for an MTV Unplugged concert in January 2014, where they sang "Don't Tell Me" and "We Can't Stop." Photo: Jeff Kravitz/2014 Jeff Kravitz
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