60 Of Madonna’s Most Iconic Fashion Moments Through The Years


If there’s one person who knows how to express herself, especially when it comes to fashion, it’s Madonna

Since the 1980s, the Queen of Pop has been pushing the envelope with her style. When she burst onto the scene, she was all about teased hair and lace, which she often paired with rosaries and crosses (a nod to her Catholic upbringing). Then we saw her go through a Marilyn Monroe phase, most notably in her “Material Girl” music video (a nod to the Monroe-starring “Gentlemen Prefer Blondes”). Then came the Blond Ambition era, followed by a slew of other reinventions. 

In honor of the Material Girl’s birthday ― she turns 60 on Aug. 16 ― we’re taking a look back at 60 of her most iconic style moments over the years. 

From her infamous Jean Paul Gaultier cone bra to her Marie Antoinette–inspired VMAs performance look to her heavenly black gown at this year’s Met Gala, Madonna really has worn it all. 

  • 1 1983
    Dave Hogan / Getty Images
    Madonna wore this bold floral number for a performance.

  • 2 1984
    David McGough / Getty Images
    This ensemble, with a lace bustier, tulle skirt and, of course, “boy toy” belt buckle is, hands down, one of Madge’s most memorable looks. She wore it for the first annual MTV Video Music Awards at Radio City Music Hall in New York City.

  • 3 1985
    Julian Wasser / Getty Images
    Eighties-era Madonna loved wearing crosses and rosaries as accessories, as she did at the American Music Awards in 1985.

  • 4 1985
    Paul Natkin / Getty Images
    The singer wore this Versace-esque ensemble during her Virgin tour.

  • 5 1985
    Jim Steinfeldt / Getty Images
    The cross motif made an appearance during Madonna’s Virgin tour. Here she is performing in Minnesota on May 21.

  • 6 1985
    Ron Galella Ltd. / Getty Images
    The singer wearing even more cross necklaces and rosaries during the after-party for the closing night of the Virgin tour.

  • 7 1986
    Vinnie Zuffante / Getty Images
    We’ll never forget the “Italians do it better” T-shirt Madonna wore — a nod to her Italian roots — for her “Papa Don’t Preach” music video, which came out that year.

  • 8 1986
    Ron Galella Ltd. / Getty Images
    Arriving at a rehearsal for the Lincoln Center Workshop production of “Goose and Tomtom” in New York City, Madonna looked undeniably cool in this white seersucker overcoat and black ensemble.

  • 9 1987
    Ron Galella / Getty Images
    The “Material Girl” singer channeled Marilyn Monroe for the 14th annual American Music Awards, where she took home a trophy for favorite pop/rock female video artist.

  • 10 1989
    Michael Ochs Archives / Getty Images
    The star perfectly mixed menswear with lingerie for a sexy yet strong look, like this outfit for a performance in Los Angeles.

  • 11 1989
    Michael Ochs Archives / Getty Images
    Long before Kim Kardashian and her sisters started rocking bike shorts while out and about, Madonna was wearing them onstage like a total boss. There’s no denying her trendsetting power.

  • 12 1990
    Frank Micelotta Archive / Getty Images
    Madonna gave the world a true fashion moment when she stepped onstage during her Blond Ambition tour wearing this Jean Paul Gaultier cone bra bodysuit. The bra, which made its runway debut in 1982, was inspired by 1950s bullet bras and the underwear-as-outerwear trend, according to Entertainment Weekly. The outfit garnered plenty of chatter and, of course, will forever be one of her most iconic looks.

  • 13 1990
    Frank Micelotta Archive / Getty Images
    The Blond Ambition tour was basically a fashion show, featuring a number of other iconic looks, including this flashy, bright fuchsia blazer. And can we just take a moment to appreciate the braid-wrapped high ponytail? The hairstyle is almost as iconic as the cone bra.

  • 14 1990
    Frank Micelotta Archive / Getty Images
    As we said, the Blond Ambition tour featured a number of memorable looks. With this ensemble, Madonna somehow made a bowler, a cone bra and chunky knee pads a lewk

  • 15 1990
    Frank Micelotta Archive / Getty Images
    Here, she rocked a polka dotted outfit, also designed by Gaultier. 

  • 16 1990
    Kevin.Mazur / INACTIVE / Getty Images
    For her performance of “Vogue” at the MTV Video Music Awards, the Queen of Pop channeled original material girl Marie Antoinette.

  • 17 1991
    David McGough / Getty Images
    The singer (here with Michael Jackson) channeled Monroe once again in a sparkling white gown, oversize furry stole and stunning diamond jewelry from Harry Winston, which she wore to the 69th Academy Awards.

  • 18 1991
    Dave Hogan / Getty Images
    The performer brought the cone bra back for the 1991 premiere of “Madonna: Truth or Dare” (titled “In Bed With Madonna” outside North America) at the Cannes Film Festival in France. She caused quite a stir with her outfit, which was a pretty loose interpretation of the festival’s formal dress code.

  • 19 1992
    Kevin.Mazur / INACTIVE / Getty Images
    To celebrate her NSFW book Sex, Madonna (here with its photographer, Steven Meisel) opted for a dirndl, which she paired with a stuffed animal. (Also note her bleached eyebrows.)

  • 20 1993
    Time & Life Pictures / Getty Images
    This sparkly two-piece outfit was part of the wardrobe for Madonna’s the Girlie Show world tour.

  • 21 1993
    Steve Eichner / Getty Images
    This intricate ensemble was also part of the Girlie Show world tour.

  • 22 1995
    Getty Images / Getty Images
    Madonna has always been one to push the boundaries with her wardrobe choices. She donned a black latex catsuit, danced in rope and appeared in other bondage gear in her video for “Human Nature,” a true sorry-not-sorry anthem.

    “The song is about basically saying don’t put me in a box, don’t pin me down, don’t tell me what I can and can’t say. It’s about breaking out of the restraints,” she said of the music video, according to Rolling Stone. “So that’s basically the point of the costume.”

  • 23 1995
    Dave Benett / Getty Images
    For her performance at the Brit Awards, the star reinvented herself once again and donned a much more angelic ensemble.

  • 24 1995
    Time & Life Pictures / Getty Images
    For the 12th annual MTV Video Music Awards, Madge went casual cool on the red carpet, pairing a pair of black satin pants with a satin shirt.

  • 25 1996
    Steve Granitz / Getty Images
    For the premiere of “Evita,” in which Madonna portrays Eva Perón, the singer channeled the former Argentine first lady’s sophisticated style.

  • 26 1997
    Ron Galella Ltd. / Getty Images
    At the Golden Globes, Madonna (with then-boyfriend Carlos Leon) proved to be the embodiment of the Dolce & Gabbana woman when she arrived wearing this lingerie-inspired dress by the Italian label.

  • 27 1997
    Ron Galella / Getty Images
    The “Ray of Light” singer went for an intergalactic look for the Gianni Versace–themed Costume Institute Gala at the Metropolitan Museum of Art in New York City.

  • 28 1998
    Frank Micelotta Archive / Getty Images
    Madonna wore this iconic denim jacket ensemble for her “Ray of Light” music video in 1998. The outfit was one of the more pared down during this period, which marked yet another reinvention for the singer that was quite different from any of her previous phases. As Dazed described it, the album, also called “Ray of Light,” feels “spiritual, elemental, and enlightened.” Around this time, she embraced Kabbala. (On her wrist, you can spot the red string bracelet associated with the religion.)

  • 29 1998
    Getty Images / Getty Images
    Madonna (with her brother Christopher Ciccone) at the Vanity Fair Oscar party on March 23 in West Hollywood. She wore a gown by designer Olivier Theyskens, which helped boost his fame in the fashion industry.

  • 30 1998
    Kevin.Mazur / INACTIVE / Getty Images
    Madge donned another Theyskens creation for the VH1 Fashion Awards. This one was a bold yellow, embellished with hook and eye detailing, which the designer told Vogue was sewn on by hand. The overall aesthetic was very Disney’s Belle–meets–Sally from “The Nightmare Before Christmas.”


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