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

HuffPost logo HuffPost 8/16/2018 Julia Brucculieri

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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

a woman wearing a pink dress © Dave Hogan / Getty Images
Madonna wore this bold floral number for a performance.

2 1984

a person wearing a dress and standing in front of a curtain © 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

a person holding a sign posing for the camera © 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

a person walking on the stage © Paul Natkin / Getty Images
The singer wore this Versace-esque ensemble during her Virgin tour.

5 1985

a woman wearing a dress © 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

a woman standing in front of a cake © 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

a little girl posing for a picture © 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

a person standing in a parking lot © 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

a woman holding a sign © 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

a woman wearing a black dress © 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

a man with a racket © 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

a person wearing a costume © 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

a girl wearing a pink dress © 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

a woman sitting on a stage © 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

a woman sitting on a stage © Frank Micelotta Archive / Getty Images
Here, she rocked a polka dotted outfit, also designed by Gaultier. 

16 1990

a person wearing a wedding dress © 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

a woman standing in front of a wedding cake © 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

a group of people posing for the camera © 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

a group of people posing for the camera © 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

a person standing on a stage © 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

Kate Moss wearing a costume © Steve Eichner / Getty Images
This intricate ensemble was also part of the Girlie Show world tour.

22 1995

a group of people posing for the camera © 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

a person posing for the camera © 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

a woman posing for a picture © 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

a person wearing a red dress © 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

a group of people posing for the camera © 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

a group of people standing in front of a crowd posing for the camera © 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

a person standing posing for the camera © 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

Christopher Ciccone et al. posing for the camera © 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

a person in a yellow dress © 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.”

31 1998

a group of people posing for the camera © Jeff Kravitz / Getty Images
Madonna went for another full gown for the Golden Globe Awards. It was definitely a far cry from her cone bra.

32 1998

a person posing for the camera © Jeff Kravitz / Getty Images
For the MTV Video Music Awards in Los Angeles, the singer opted for red snakeskin-effect pants and a long sequined vest.

33 1999

a person in a red dress © Frank Micelotta Archive / Getty Images
Madonna wore this striking red kimono, another Gaultier creation, for her “Nothing Really Matters” music video. She took the same ensemble to the stage for her performance at that year’s Grammy Awards.

34 2000

a woman wearing a black dress © KMazur / Getty Images
Britney Spears burst onto the scene in the late ’90s and often cited Madonna as her top inspiration. The “Frozen” singer was a fan of Spears’ and at reportedly became obsessed with wearing Britney T-shirts, thinking they would bring her luck.

35 2000

a person in a red dress © Stephane Cardinale / Corbis / Getty Images
Madge wore this western-inspired ensemble to the MTV Europe Music Awards in Stockholm.

36 2001

Guy Ritchie et al. posing for the camera © Chris Weeks / Getty Images
Madonna made sure everyone knew she was Mrs. Guy Ritchie when she walked the red carpet at the “Snatch” premiere, wearing this bridal-white crystal-encrusted blazer. The singer and director tied the knot in December the previous year.

37 2003

a woman standing in front of a crowd posing for the camera © Frank Micelotta / Getty Images
Who can forget this MTV VMAs moment? Madonna swapped spit with Spears and Christina Aguilera in front of the world, and while the quick kisses were definitely the talk of the town, what the women were wearing was just as much a part of the moment.

38 2004

a person standing next to a body of water © KMazur / Getty Images
Madonna gave a nod to her famous “Italians do it better” T-shirt with this “Kabbalists do it better” version.

39 2005

a person holding a sign posing for the camera © David Lodge / Getty Images
For her “Confessions on a Dance Floor” phase, which was heavily disco inspired, she favored Farrah Fawcett–style hair and plenty of period dancewear.

40 2005

a person posing for the camera © Dave M. Benett / Getty Images
The singer wore this white tailored outfit for her performance at “Live 8” in London’s Hyde Park on July 2.

41 2006

© KMazur / Getty Images
For her performance at the Grammys, Madonna donned a light purple outfit resembling her bodysuit in the “Hung Up” video while echoing her 2003 VMAs ensemble.

42 2007

Guy Ritchie et al. posing for a picture © Chris Farina / Getty Images
Madonna wore this classic black gown, with modern bondage-inspired straps, to the Vanity Fair Oscar party with Ritchie.

43 2009

Guy Oseary standing in a room © Kevin Mazur / Getty Images
For “The Model as Muse: Embodying Fashion” Costume Institute Gala, the singer donned this Louis Vuitton ensemble, complete with bunny ears. It’s the same outfit she wore in the label’s fall/winter ad campaign that year.

44 2011

Lourdes Leon standing posing for the camera © Craig Barritt / Getty Images
She took daughter Lourdes Leon with her to the Vanity Fair Oscar party, where the singer opted for the sheer lace number with a black bodysuit underneath.

45 2011

a woman sitting on a rug © Kevin Mazur / Getty Images
This starry blue Stella McCartney gown is perhaps one of Madonna’s most conventionally pretty outfits. She wore it for that year’s Met Gala, which honored Alexander McQueen, in New York City.

46 2011

a person wearing a red dress © Venturelli / Getty Images
The star went for another very pretty look for the Venice Film Festival. This gown was by Vionnet.

47 2012

Madonna standing in front of a sign posing for the camera © Steve Granitz / Getty Images
Madonna wearing a Reem Acra dress at the 69th Annual Golden Globe Awards in Beverly Hills.

48 2012

a group of people wearing costumes © Kevin Mazur / Getty Images
The singer no doubt turned heads with her impressive Super Bowl performance outfits, including this gilded custom Givenchy number (by Riccardo Tisci).

49 2012

a person posing for the camera © Kevin Mazur / Getty Images
Madonna enlisted Gaultier once again to design the costumes for her MDNA tour. Naturally, there was an updated cone bra, which is just as iconic as the original.

50 2012

a person wearing a costume © Kevin Mazur / Getty Images
Her wardrobe for the MDNA tour also included this red and white cheerleader-inspired ensemble.

51 2013

a woman wearing a costume © Jamie McCarthy / Getty Images
Madonna worked with Tisci once again for this plaid outfit, which she wore for the punk-themed Met Gala in New York.

52 2014

Madonna wearing a suit and tie © Jason Merritt / Getty Images
Madge took her son David Banda Mwale Ciccone Ritchie to the 56th Grammy Awards in Los Angeles, where they wore matching suits.

53 2015

a person posing for a picture © Jason Merritt / Getty Images
The “Girl Gone Wild” singer unleashed her inner matador with this heavily embellished ensemble at the Grammys in LA. It was cheeky, to say the least.

54 2015

a couple of people posing for the camera © Kevork Djansezian / Getty Images
For her Grammys performance, Madonna stuck with the matador theme with this red number.

55 2015

Madonna standing in front of a crowd © Dimitrios Kambouris / Getty Images
For her Met Gala appearance, Madge rocked this black gown by designer Jeremy Scott.

56 2016

a person standing in front of a crowd posing for the camera © Kevin Mazur / Getty Images
Madonna’s bum made another red carpet appearance at the Met Gala, thanks to this sheer gown by Tisci for Givenchy.

57 2016

a person sitting on a elephant © JB Lacroix / Getty Images
The icon paid tribute to music legend Prince at the Billboard Music Awards. Fittingly, she wore a purple suit, inspired by the iconic one worn by the “Purple Rain” singer.

58 2017

a group of people standing next to a woman © Paul Morigi / Getty Images
Never one to shy away from talking about politics, Madonna showed up at the Women’s March on Washington in 2017, wearing her own version of the popular pussy hat.

59 2017

a person holding a birthday cake © John Shearer / Getty Images
For the Met Gala, Madonna wore another gown by Scott, this time in camo chic. She also appeared to be wearing a grill in her mouth.

60 2018

a woman wearing a black dress © John Shearer / Getty Images
For this year’s Catholicism-themed Met Gala, Madonna wore another Gaultier gown. It didn’t involve a cone bra, but it definitely made a statement with its sheer cross cutout on the bodice.
This article originally appeared on HuffPost.
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