No pop diva has reinvented her fashion image with the consistency and creativity of Madonna. Madge, who is this year's Woman of the Year thanks to an outstanding year of touring, emerged on the scene in the early '80s as a street-smart "Boy Toy".
Over the course of her 30-plus year career, she evolved into a fashion-forward icon whose sense of style became as influential as her chart-topping tunes. "Mostly what Madonna [wears] is an evolution of what is relevant at the time," said her stylist of over 20 years, Arianne Phillips, in an exclusive interview with Billboard. "The visuals reflect the music in a kind of seamless marriage of her point of view." In celebration of Madonna, we present 55 of her most unforgettable outfits, from jaw-dropping Jean-Paul Gaultier corsets to elegant Dolce & Gabbana gowns.
Madonna struck a pose in New York City, rocking the '80s thrift-shop, club-kid look -- complete with an endless amount of rubber bracelets and her trademark hair ribbon -- that would inspire the army of Madonna wannabes who followed the emerging star's every move.
Sept. 14, 1984
Madonna looked both naughty and nice when she hit the stage of the inaugural MTV Video Music Awards for her debut performance of "Like a Virgin." The lacy wedding dress and infamous "Boy Toy" belt turned heads around the world and remains one of her most iconic looks.
Jan. 28, 1985
No one had to ask who's that girl when Madonna hit the red carpet of the American Music Awards in a sultry Jean-Paul Gaultier corset dress and her signature strands of beads, crucifixes and pearls. It was edgy, with just a hint of the elegance to come.
July 13, 1985
Madonna performed for a packed house at the Live Aid benefit concert at JFK Stadium in Philadelphia, looking a bit like a gypsy woman gone glam. It was the first time since making it big Madonna stripped away the blond and let her natural roots show.
April 17, 1986
Madonna trimmed her teased locks and rocked a dashing ball gown when she attended the At Close Range premiere with then-husband Sean Penn.
May 1, 1986
Madonna debuted a brand-new, understated "bad girl" look during the filming of her "Papa Don't Preach" music video. Her cropped, peroxide-bleached hair and black biker jacket showed a different flavor of her edgy street style.
July 31, 1987
Madonna's love for bustiers began to bubble up as she performed in Chicago during the "Who's That Girl" world tour. The black leather and zipper-detailed one piece mimicked the eye-popping peep-show outfit made famous in her "Open Your Heart" video.
Aug. 6, 1987
Madonna left her grungy look behind and went for full-on glamor at the Who's That Girl film premiere. Madge strutted down the red carpet in a silver-lined glass-bugle beaded dress and a killer blonde-bombshell cut that garnered her more that one comparison to the late Marilyn Monroe.
June 25, 1990
Get the points? During her "Blonde Ambition" tour, Madonna revealed some of the most ambitious outfits of her career. This show-stopping pink cone bra ensemble, designed by her frequent fashion collaborator Jean-Paul Gaultier, remains one of her most infamous looks.
Sept. 12, 1990
Madonna turned back the clock and embodied Marie Antoinette as she performed her smash hit "Vogue" on the MTV Video Music Awards. The Victorian-era costume was one actually worn by Glenn Close in the 1998 film Dangerous Liaisons.
March 25, 1991
Madonna arrived to the 63rd annual Academy Awards afterparty at Spago's on the arm of date Michael Jackson, dripping with $20 million worth of Harry Winston diamonds and channeling screen siren Marilyn Monroe. Diamonds really are a girl's best friend.
May 8, 1991
Backup singers Donna De Lory and Niki Harris flanked the Queen of Pop at the New York City premiere of Madonna's Truth or Dare documentary at the Ziegfeld Theatre. The singer rocked a glittering Dolce & Gabbana bustier littered with multi-colored jewels like only she could.
May 16, 1991
Another premiere, another outrageous outfit. A brunette Madge attended the Cannes Film Festival in France looking like a Catholic schoolgirl with an edgy twist in a Jean-Paul Gaultier miniskirt and thigh-high stockings.
Sept. 24, 1992
Madonna let it all hang out -- once again, with the help of Jean-Paul Gaultier -- at a fashion show he threw to Benefit AmFar. The singer took to the catwalk bare-breasted while the designer himself escorted her down the runway. A shocking pair, no matter how you look at it.
Oct. 15, 1992
Madge dropped jaws again as she threw a soiree for the premiere of her scandalous coffee-table book of erotica, "Sex." The diva arrived looking like a Little Bo Peep who practiced a little S&M on the side.
Oct. 14, 1993
During her sexually charged Girlie Show tour -- seen here at New York's Madison Square Garden -- Madonna opened the show in an enticing, Indian-inspired stage costume drenched in glitter, religious symbols and plenty of sex appeal.
April 26 1994
At the Los Angeles premiere of the film "With Honors" -- to which she contributed the song "I'll Remember" -- Madonna put the raunchiness to rest and went for a more bohemian look in a blue crop top and billowing, patterned dress.
Sept. 7, 1994
Madonna did another style 180 at the 1994 MTV Video Music Awards Madonna and served up flapper-chic style in a pale green sculpted dress, accented by a platinum-blond, finger-wave hairdo.
March 18, 1995
Madonna turned the glamour all the way back up at her "Bedtime Story" dance party at NYC's Roxy nightclub, where she wore a white slip dress and leopard-print overcoat. Meow.
Sept. 7 1995
At the 12th annual MTV Video Music Awards, Madonna kept it cool and current, rocking a Chanel silk blouse that was subtly unbuttoned enough to reveal a sheer bra.
Dec. 14, 1996
During the premiere of her film "Evita" at L.A.'s Shrine Auditorium, Madonna paid homage to her hero, Eva Peron, in a dazzling ruby-red and very regal-looking Versace number. Long Live the Queen!
Jan. 19, 1997
At the 1997 Golden Globe Awards (where she won Best Musical or Comedy Actress for her role in 'Evita') Madonna, who'd recently given birth to her first child, went Hollywood glam, wearing a sleek Dolce & Gabbana black gown that highlighted the curves of her post-birth body.
Sept. 9, 1998
At the 1998 Academy Awards, Madonna walked the red carpet wearing one of Jean-Paul Gaultier's chic skirts paired with a black silk over-garment by Olivier Theyskens, resulting in a look that was both poetic and graceful.
Oct. 23, 1998
After toning down her look for a couple years, Madonna stunned at the 1998 VH1 Fashion Awards in this Olivier Theyskens (unmellow) yellow gown, accented by her gothic, jet-black hair. Let's just say the press weren't big fans of this particular look.
Oct. 23, 1998
Madonna went in an entirely different direction for her second VH1 Fashion Awards outfit -- a traditional royal-blue sari that referenced her growing interest in Eastern cultures and religions.
Dec. 10, 1998
Madonna arrived at the 9th annual Fire and Ice Ball at Universal Studios in Los Angeles looking like she just put her whip down on the night stand. The singer was packaged in a bondage-inspired black leather gown with cuts running throughout, looking more like a heavy-metal princess than a pop queen.
Feb. 24, 1999
During her performance of "Nothing Really Matters," Madonna rocked the stage at the 41st Annual Grammy Awards in a bright-red Jean-Paul Gaultier kimono -- a nod to her obsession with Asian culture.
July 21, 2001
Madonna greets fans with a brand-new punk aesthetic. Here, she opens her Drowned World Tour in Philadelphia wearing a plaid kilt and coordinated top, paired with leather bondage pants.
Jan. 18, 2001
At the premiere of 'Snatch,' a film directed by then-husband Guy Ritchie, Madonna rocked a white suite with "Mrs. Ritchie" plastered across the back in rhinestones. We wonder who really wore the pants in that relationship.
April 22, 2003
Even when Madonna dresses down, she still manages to turn everyone's head. Madge performed songs from her album 'American Life' at the MTV studios in New York City in an unfussy striped knit shirt and flared black slacks -- a look that oddly felt more French than American.
Jan. 24, 2004
Madonna took a turn for the playful at the NRJ Music Awards ceremony in Cannes, France, where she performed in a playful green dress covered with a curious star pattern.
Sept. 8 2004
The return of the corset! Madge kicked off her Re-Invention Tour at the Gereldome in the Netherlands wearing a comically embellished outfit that paid homage to several of her most famous looks at once.
Nov. 3, 2005
At the MTV Europe Music Awards in Lisbon, Portugal, Madonna revealed her new 'Hung Up' disco phase in a purple bomber jacket and matching purple boots.
Nov. 3, 2005
Backstage at the MTV European Music Awards, Madonna continues to pay homage to the '70s in this gold and burnt-umber-colored velvet gown.
Dec. 7, 2005
Madonna rocks a glittering sequenced sleeves and genie-pants - along with her ever-present purple leotard -- during a press conference in Tokyo, Japan hailing her 'Confessions on a Dance Floor' album. Hail to the disco queen.
Feb. 8, 2006
In the press room at the 48th Annual Grammy Awards in Los Angeles, Madonna rocked this badass black dress with crystal detailing.
March 5, 2006
Madge looked pretty in pink at the Vanity Fair Oscar Party at Morton's in West Hollywood in a figure-hugging pink Versace gown and studded heals.
Jan. 11, 2007
Madonna channeled her masculine side during the 'Arthur and The Invisibles' screening at Tribeca Cinemas in New York City. The Material Girl rocked a tame yet sophisticated black blazer, white blouse and Chanel belt.
March 10, 2008
The queen of pop's countless contributions to music led to her induction into the Rock and Roll Hall of Fame in 2008. During the ceremony, held at New York's Waldorf Astoria, Madonna rocked a black dress with white stripped detailing that was sheer in all the right places.
May 1, 2008
Madonna was spotted outside of BET's '106 & Park' at CBS Studios in New York City in this pimp-tastic ensemble that featured a black fur coat, black boots, and an endless supply of gold chains.
Nov. 19, 2008
Only Madonna could get away with wearing head-to-toe Louis Vuitton to a Gucci event. The singer rocked a green-feathered mini from LV's spring 2009 collection at Gucci's launch of the Tattoo Heart Collection to Benefit UNICEF dinner at The Plaza in New York City.
May 4, 2009
Styled by Marc Jacobs himself, Madonna rocked a Louis Vuitton autumn/winter 2009-10 blue dress, over-the-knee boots and custom haute couture bunny ears at 'The Model as Muse: Embodying Fashion' Costume Institute Gala at The Metropolitan Museum of Art in New York City. Though many considered her one of the event's worst-dressed at the time, it was a look that made headlines across the world
Nov. 3, 2010
Though she's a mother of four, Madonna proved she hadn't lost her edge when she turned up to the Fashion Delivers Gala in New York wearing a pair of over-the-knee Stella McCartney PVC boots and a silver crocheted tunic.
Feb. 27, 2011
At the Vanity Fair Oscar party in West Hollywood, Madonna rocked a deeply slit, sheer lace and feathered gown, worn over a black leotard that was polished off with her signature fishnets and a fur vest. Her daughter Lourdes Leon, who also looked stunning in an AllSaints Aztec mini, proved to be mom's most flattering red carpet accessory.
May 2, 2011
Madonna truly looks like a queen in this decadent Stella McCartney dress, accessorized with Cartier jewelry and Sergio Rossi heels at the 'Alexander McQueen: Savage Beauty' costume institute gala at The Metropolitan Museum of Art in New York City.
Sept. 1, 2011
Covered in red butterflies, Madonna stunned in this regal Vionnet gown to promote her film 'W.E.' at the 2011 Venice Film Festival. Footnote: the costumes for the film were taken from the archives of the same designer.
Sept. 2, 2011
In Venice, Italy -- the same city where Madge shot her 'Like a Virgin' video 27 years earlier -- Madonna attended the 2011 Gucci Award For Women in Cinema at Hotel Cipriani, wearing a bespoke Gucci Georgette evening gown with jet and gold metal details at the waist.
Jan. 15, 2012
Now a two-time Golden Globe winner, Madonna looked ready for a couture battle in this metallic, Reem Acra pre-autumn/winter 2012-13 dress at the Beverly Hills ceremony.
Jan. 23, 2012
Madonna, now a celebrated director, attends the premiere of her film 'W.E.' wearing a black Marchesa gown at the Ziegfeld Theater in New York City. No offense to either Marchesa and Madonna, but we're not sure this is Madge's finest fashion hour.
Feb. 5, 2012
All eyes were on the 50-yard line when Madonna took center stage at the 2012 Super Bowl half-time show, wearing Givenchy Haute Couture by Riccardo Tisci, topped off by a glittering Cleopatra crown. The medley of hits she performed for the 114 million fans watching reminded the world why she remains one of pop's most electrifying artists, and her stunning outfit recalled why she remains one of music's most fashion-forward artists. We can't wait to see what outrageous outfits she still has up her always stylish sleeve.
May 6, 2013
Madonna steals the show at the “PUNK: Chaos to Couture” gala at the New York Metropolitan Museum of art in a custom Ricardo Tisci plaid and silver embellished blazer dress paired with fishnets, black leather loves, a blunt cut black wig and hot pink pumps.
May 17, 2013
Madge donned a (mostly) traditional Boy Scout uniform at the 24th annual GLAAD Awards, in defiance of the organization’s ban on gay scouts and scout leaders. "I wanted to be a Boy Scout but they wouldn't let me join... I can build a fire. I know how to pitch a tent... Most importantly, I know how to scout for boys!"
May 19, 2013
Madonna made sure everyone knew she was the biggest star in the room when she turned up to accept the Top Touring Artist award at the 2013 Billboard Music Awards. Madge accepted the honor in a provocative outfit made by Givenchy’s Riccardo Tisci, which included black shredded fishnets, a garter belt and black briefs.
June 18, 2013
Madonna arrived to the New York premiere of her “Madonna: The MDNA Tour” film premiere decked out in a classic black tuxedo with white waistcoat and bow tie. The outfit was a nod to iconic actress and singer Marlene Dietrich.
Jan. 26, 2014
“We’re both working the Ralph Lauren angle,” Madonna told host Grammys red carpet host Ryan Seacrest as she wonderfully blurred gender lines in a dapper Ralph Lauren suit. “He dressed me tonight,” Madge said of her son David choosing her Grammys look. “He wanted me to dress like him, so I obeyed him.”
Feb. 8, 2015
Madonna channels a bull-fighter at the Grammys, a look she'd hone over her next few appearances.
Feb. 25, 2015
Madonna took her bull-fighter look to another level during her Brit Awards performance -- but the cape ended up being a bit of a work hazard, which caused her to fall down the stairs during her song.
Feb. 25, 2015
When Madonna took off the cape, though, her S&M-inspired bull-fighting outfit stole the show.