Ranking Madonna’s 19 most standout looks from her 4-decades-long pop music career

Madonna has rocked many eccentric looks throughout her 40-year career. Ross Marino/Icon and Image/Getty Images, George Pimentel/WireImage, Gie Knaeps/Getty Images A biopic is in the works about Madonna’s launch as a solo music artist in 1981, Variety reports. To celebrate the news, we’re looking through some her most iconic — and daring — looks of all time.

Here are 19 glamorous and grungy Madonna outfits that we’ve ranked from least to most iconic.   In 2011, Madonna attended the Met Gala in a silk, embroidered, Stella McCartney gown that was elegant but ultimately underwhelming. Madonna at the 2011 Met Gala.

Kevin Mazur/WireImageIf there one thing Madonna is all about, it’s making a splash. But when she wore this sleek Stella McCartney gown for her 2011 appearance at the Met Gala, it came across as largely forgettable to us. While she appeared mature and elegant, it just didn’t scream “Madonna” like most people would expect.

She did, however, incorporate her signature red lipstick, giving a nod to that classic “in your face” Madonna style that we all know and love. The Queen of Pop’s outfit for the European Music Awards in 2005 was sporty, but not as daring as other signature looks. Madonna at the 2005 MTV European Music Awards in Lisbon.

Toni Anne Barson/WireImageFor any other star, fish net tights and knee-high, leather boots could be classified as daring. For an icon like Madonna, this is practically tame.  At the time, the pop star was performing her tenth studio album, “Confessions on a Dance floor,” and this ensemble became her go-to during promotion, Harpers Bazaar reported.

 The purple bomber jacket with her caramel hairstyle and oversize sunglasses created a youthful, fun look, but there have been much better Madonna outfits over the years.  As the new Mrs. Ritchie, her diamante-emblazoned jacket was playful, if kitschy.

Madonna and Guy Ritchie at the premiere of “Snatch” in 2001. Chris Weeks/Liaison, SGranitz/WireImageIn 2001, Madonna attended the premiere of “Snatch,” a film directed by her then-husband Guy Ritchie, according to The Telegraph. For the event, she opted for a cream-colored pantsuit, with the bedazzled blazer reading “Mrs Ritchie” in rhinestones.

 The former couple had just tied the knot the previous month, making her outfit a playful choice for a newlywed. But we found it a bit garish, and overall, the whole look feels pedestrian compared to other famous Madonna ensembles.  Madonna showed off her love of androgynous fashion with this outfit worn at the Live Aid benefit concert in 1985.

Madonna takes part in the Live Aid benefit concert at the John F. Kennedy Stadium in Philadelphia, in July 1985. Vinnie Zuffante/Michael Ochs Archives/Getty ImagesMadonna’s Live Aid benefit outfit consisted of flowery pants with a pale-green, oversized waistcoat and jacket — classic 1980s’ fashion.

 The overall effect felt cute for the young star. While the look itself doesn’t appear particularly groundbreaking, it did have a lasting effect on Madonna’s role as a fashion icon: it encapsulated the boundaries she would soon be pushing when it came to traditional masculine and feminine clothing, and it foreshadowed some of her famous fashion moments to come.  Madonna went for a seductive look featuring an eye patch during her Eurovision performance in 2019, which invited parallels with the then-popular television show “Game of Thrones.

“Madonna performs after the 64th Annual Eurovision Song Contest in 2019. Michael Campanella/Getty ImagesFor her performance at the Eurovision Song Contest in 2019, Madonna rocked a leather bodysuit with silver embellishments, tulle sleeves, fish net tights, and thigh-high leather boots. Accessories included a silver crown and a much-discussed black eye patch emblazoned with the letter “X.

“Following the performance, actor Pilou Asbaek, who played Euron Greyjoy in “Game of Thrones,” tweeted a comparison of her ensemble to the costume he wore for the show. However, weeks later, Madonna explained to TODAY’s Harry Smith that the letter on the eye patch was a reference to the persona she created for her fourteenth studio album: “Madame X. “Madonna wore a revealing version of a traditional German dirndl dress to the 1992 launch for her book, “Sex.

“Madonna at the book party for her novel, “Sex. “Kevin Mazur Archive/WireImageIn 1992, Madonna arrived to the launch party for her book, “Sex,” wearing a spin on a traditional German dirndl dress, often worn by partygoers at Oktoberfest events around the world. Her version had a low-cut neckline, and she completed the look with her hair tied up in two buns.

She even bleached her eyebrows. Publications including People Magazine reported that she was going for a sexy version of a Little Bo Peep costume, which explains the stuffed sheep toy in her hand. It wouldn’t have been unlike Madonna to take something generally considered innocent and give it a provactive twist.

She is ever the one to push boundaries, even as an author. Despite the scandalous nature of “Sex,” the book sold 150,000 copies the first day, according to Newsweek. One of Madonna’s 1991 Cannes Film Festival outfits consisted of a grey tutu paired with a blazer.

Madonna at Cannes in 1991. ARNAL/GARCIA/PICOT/Gamma-Rapho via Getty ImagesOne of the rare moments when Madonna walked the red capret without her signature bleach-blonde hair was during the Cannes Film Festival in 1991.  While in the south of France, she wore this tutu and blazer combo, paired with white, knee-length socks, and chunky black boots.

It’s a high-point of school-uniform-meets-punk-rock, a look Madonna is known for pulling off in the best ways possible.  Madonna and her son, David Banda, looked sharp in matching Ralph Lauren suits at the Grammy Awards in 2014. Madonna and her son, David Banda, at the 2014 Grammy Awards.

Christopher Polk/Getty Images for NARASMadonna and her son, David Banda, opted for immaculately tailored, coordinating suits for their appearance at the Grammy Awards in 2014. Both were designed by Ralph Lauren as part of the Spring/Summer 2014 collection, she told Ryan Seacrest for E! News on the red carpet. The pop singer completed her look with a bowler style hat, while her son topped his outfit off with a fedora.

 Adorably, Madonna also credited Banda with the idea to wear matching outfits. “I followed his lead. He dressed me tonight,” she said.

“He wanted me to dress like him, so I obeyed him. “Not all iconic looks are memorable for the right reasons, and Madonna’s kimono-inspired look from the Grammy Awards, in 1999, is a prime example. Madonna performs at the 41st Annual Grammy Awards in 1999.

Ron Wolfson/Getty ImagesWas this look memorable? Yes. That said, by today’s standards Madonna’s decision to wear a Jean Paul Gaultier-designed, blood-red kimono — a traditional garment rooted in Japanese culture — probably wouldn’t fly when it comes to conversations on cultural appropriation.  Looking back, she also didn’t do herself any favors by mimicking geisha makeup, which consists of white foundation known in Japan as “oshiroi,” according to History.

com. It’s far from the only time that Madonna has borrowed customary garments and styles from other countries and cultures. A few examples include her sporting a bindi on her forehead while performing “Shanti-Ashtangi” at the VMAs in 1998, and later in 2014, wearing a niqab on Instagram.

That sparked a level of public backlash and criticism about cultural appropriation relatively unheard of in her earlier career.  Madonna has always pushed the envelope, but sometimes she may go too far.  Madonna said her Met Gala outfit in 2016 was “a political statement” and it certainly had people talking.

Madonna attends the Met Gala in 2016. George Pimentel/WireImage, Larry Busacca/Getty ImagesFor the Met Gala in 2016, Madonna wore a sheer Givenchy gown that exposed her breasts and butt. There was a powerful message behind her revealing style choice.

Captioning for an Instagram post shared two days after the event, she wrote an explanation for her outfit, which wasn’t as scandalous as it looks:”We have fought and continue to fight for civil rights and gay rights around the world. When it comes to Women’s rights we are still in the dark ages. My dress at the Met Ball was a political statement as well as a fashion statement.

The fact that people actually believe a woman is not allowed to express her sexuality and be adventurous past a certain age is proof that we still live in an age-ist and sexist society. I have never thought in a limited way and I’m not going to start. “Madonna brought the drama to the 1998 VH1 Vogue Fashion Awards by wearing this vampy, yellow corseted gown.

Madonna backstage at the 1998 VH1 Vogue Fashion Awards in New York City. Frank Micelotta/ImageDirectMadonna channeled a vampire queen with her jet-black hair, dramatic jewelry, and cherry red lipstick for the VH1 Vogue Fashion Awards in 1998.  For the event, she wore a bright-yellow, corseted gown by designer Olivier Theyskens, which featured long sleeves, strong shoulders, and a sharp A-line skirt that accented the pop star’s waistline.

Some say that she was channeling Belle from “Beauty and the Beast. ” If so, Madonna, of course, wore a version that was much spicier and more dramatic. Madonna wore a feminine, Versace dress to Vanity Fair’s Academy Awards afterparty in 2006.

Madonna leaves the Vanity Fair Oscar Party at Mortons on March 5, 2006, in West Hollywood. Mark Mainz/Getty ImagesMadonna’s bubblegum-pink, Versace gown perfectly accentuated her figure while also appearing to be flowy and comfortable. She paired the look with sparkly stilettos and a sleek hairdo.

 According to Interview Magazine’s 2006 interview with Lindsay Lohan, who also wore Versace to the event, the two women had a “little fashion moment” at the party. “She was wearing Versace and she goes to Guy [Ritchie, Madonna’s husband], ‘Who’s wearing better Versace?'” Lohan said to the magazine of the interaction. “And he didn’t say anything.

Mine was this elegant, long gown. Hers was elegant as well. It was beautiful, pink.

I’d never seen Madonna in pale pink, and she looked gorgeous. “Madonna’s costume designer credited her with developing the idea of wearing a Marie Antoinette-style gown while performing “Vogue” at the MTV Awards in 1990. Madonna performing “Vogue” at the 1990 MTV Awards.

Frank Micelotta/ImageDirectWhile performing “Vogue” at the 1990 MTV Awards, Madonna wore a spectacular, 18th-century period costume complete with a towering wig and feathers.  According to a TODAY interview, Marlene Stewart, the costume designer who worked with Madonna on the look, said that Madonna helped conceptualize the idea.  “We know historically that the French were the biggest posers, and it’s the whole idea of voguing and posing,” Stewart said in the interview of the connection between the song and the look.

“It was the perfect transition. I suggested this French court situation with Marie Antoinette. It’s really one of the origins, right? All they did was, ‘Strike a pose.

‘”The performance by Britney Spears, Madonna, and Christina Aguilera at the MTV Video Music Awards in 2003 was memorable for many reasons, including style. Britney Spears, Madonna, and Christina Aguilera during MTV VMAs in 2003. Chris Polk/FilmMagicWho could forget the infamous kiss shared between Madonna and Britney Spears at the 2003 VMAs?What made the moment that much more memorable were the wedding-inspired outfits worn by all three stars.

Spears and Christina Aguilera’s white looks echoed wedding gowns and perfectly off-set Madonna’s all-black “groom” outfit, which consisted of thigh-high leather boots, black leggings, a long suit jacket, and a top hat. Madonna was the epitome of 1980s fashion with this colorful ensemble worn during her “Virgin Tour” in 1985. Madonna on stage during the “Virgin Tour” in 1985.

Jim Steinfeldt/Michael Ochs Archives/Getty Images, Ross Marino/Icon and Image/Getty ImagesIt doesn’t get more 1980s than Madonna’s “Virgin Tour” outfits. For this particular stage look, she wore cropped, purple, lace leggings with a belted miniskirt and an ornate bomber jacket over a crop top. She capped it off with a big, purple bow in her curled hair.

 If you’ve ever been to 1980s-themed party, we’re sure you’ve seen someone rocking something akin to this look.  The Queen of Pop went for regal goth with her red carpet appearance at the Met Gala in 2018. Madonna attends the Met Gala in 2018.

John Lamparski/Getty ImagesMadonna is no stranger to fashionable choices with religious references, and her 2018 Met Gala look was no different.  The gala’s theme was “Heavenly Bodies: Fashion and the Catholic Imagination,” which Madonna took very literally — and rightfully so, as the dress code echoed all-things church. She opted for a voluminous, gothic-style, Jean Paul Gaultier gown with a black, net veil.

Vogue reported the veil was held in place by bejeweled crosses and rosaries.  She also carried a bouquet of black flowers. Possibly most standout was her silver crown decorated with a crucifix, an obvious reference to religous sculptures and depictions of the Virgin Mary in Catholic churches.

 Long before Kim Kardashian, Madonna took notes from Marilyn Monroe, including for Madonna’s 1991 Oscar’s afterparty look. Madonna and Michael Jackson at the Academy Awards afterparty in 1991. Ron Galella/Ron Galella Collection via Getty ImagesChanneling Marilyn Monroe, Madonna was a vision of Old Hollywood glamour in the photographs taken of her leaving the 1991 Oscars afterparty, hand-in-hand with Michael Jackson.

The silver dress, which Madonna paired with a white fur stole and a glittery clutch, was designed by Monroe-favorite Bob Mackie, according to The Times of London. It was Mackie who drew the original sketches for 1962 Jean Louis gown that Monroe wore to sing “Happy Birthday” to President John F. Kennedy as well as the dress that Kim Kardashian wore recently to the 2022 Met Gala.

 We respect her nod to fashion history.  In 1984, her “Like a Virgin” Video Music Awards look blended punk and fairytale wedding perfectly. Madonna poses at the first MTV VMAs in 1984, held at Radio City Music Hall in New York City.

Sonia Moskowitz/Getty ImagesWho thought wedding dresses could be punk? Madonna, that’s who. Her VMAs outfit, worn during her performance of “Like a Virgin” in 1984, subverted the purity of the white wedding dress with the addition of daring details and piles of statement jewelry. Her tulle skirt featured heart appliques, and the lace corset added to the provocative nature of the entire ensemble.

 The standout feature, though, was the chunky, metallic belt reading “Boy Toy. “The performance also sealed her reputation as a pop star legend. In addition to the iconic outfit and suggestive choreography, a wardrobe malfunction lead to the accidental appearance of her underwear, according to MTV.

com. Some members of her team felt she had ended her career before it began, but the slip-up worked in Madonna’s favor. Viewers loved it.

She has been in the limelight ever since. Nothing screams Madonna as much as the busty, pale-pink leotard she wore throughout her Blonde Ambition tour in 1990. Madonna on the Blonde Ambition tour in 1990.

Gie Knaeps/Getty ImagesAccording to Vogue, Madonna kicked off the first night of her Blonde Ambition tour wearing a pinstripe suit before revealing the iconic bodysuit designed by Jean Paul Gaultier.  The sharpness of the cones and the soft pink tones of the bodysuit echoed Madonna’s love of androgyny and provocativeness. If there is one clothing item that sums up her approach to fashion, it’s this.

In a 2001 interview with The New York Times, Gaultier talked about that early collaboration. “She knew what she wanted: a pinstripe suit, the feminine corsetry,” he said. “Madonna likes my clothes because they combine the masculine and the feminine.

“The costume would also begin years of creative partnership between Gaultier and Madonna.  Today, you can still find references to this look in mainstream culture. Just Google “Madonna Blonde Ambition bodysuit” and you’ll find a few versions you can wear yourself.

 Read the original article on Insider.