Madonna’s Best Style Evolution Moments: Her Most Iconic Fashion Photos


Madonna is nothing short of a style icon. Getty Images

From the moment that she released her self-titled debut album in 1983, Madonna has shown audiences that she understands the power of a multifaceted performer—and she’s been delivering ever since. Whether through multimillion-dollar world tours or on-screen in films, the Michigan native has become so influential (and at times, controversial) that she’s surely earned her moniker as the Queen of Pop.

On stage, fashion has always played a major part in the singer’s career, serving as a tool to help create looks that are as memorable as her music. Drawing inspiration from various periods in history as well as from religion, Madonna’s fashion choices have included everything from feminine lace- and lingerie-inspired looks to more masculine suiting.

And while fashion has undoubtedly been at the center of Madonna’s reinventions over the past 40-plus years, offstage, she’s also played muse, model and even creator in the design world. She championed designers like Olivier Theyskens and fashion houses like Dolce & Gabbana at the start of their respective careers, and strutted the runway for Jean Paul Gaultier (her most constant fashion collaborator) on multiple occasions. No stranger to style campaigns, Madonna has starred as the face of advertisements for luxury fashion houses like Versace, Dolce & Gabbana and Louis Vuitton, and she’s ventured out into the design world herself, too. First collaborating with H&M on her M by Madonna fashion line in 2007, Madonna and her daughter Lourdes later launched the teen clothing brand Material Girl in 2010.

Still, it’s her sartorial choices for music videos and live performances that have been the most enduring. From the signature Jean Paul Gaultier cone bra that catapulted her to fashion icon status, to the current barely-there ensembles that prove she still knows how to cause a stir, take a look back at the fashion moments that have helped to define Madonna’s career.

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Madonna wearing a white dress with jewerly
Madonna. Getty Images

1984, MTV VMAs

From the start, Madonna wasn’t afraid of making waves, taking to the stage at the first-ever MTV Video Music Awards for a now-infamous performance of “Like a Virgin.” Wearing a lingerie-inspired wedding dress, complete with white lace gloves, strings of pearls and her ‘Boy Toy’ belt, Madonna’s performance caused such a scandal that she says it nearly ended her career at the time. Of course, as history shows, the moment made Madonna a household name, and was eventually recreated in another iconic instance nearly two decades later.

Madonna wearing a black dress with layered necklaces
Huey Lewis and Madonna. Ron Galella Collection via Getty

1985, American Music Awards

The 1985 American Music Awards marked the beginning of a style (and partnership) that became synonymous with Madonna. The “Material Girl” singer wore a corset-style top by Jean Paul Gaultier, and the mini cone-shaped bra hinted at things to come from the duo. The look was completed with a mix of crucifix necklaces and rosary beads, and because it was the ‘80s, Madonna’s bleached blonde hair was pulled back into a ponytail with a scrunchie.

Madonna wearing a black bodysuit
Madonna. Getty Images

1987, ‘Who’s That Girl’ Tour

Two years later, Madonna went blonder and shorter with a platinum pixie for the “Who’s That Girl” tour, but her sartorial tastes stayed the same: a bustier leotard with fishnet stockings.

Madonna wearing a shiny dress with red lip
Madonna. Ron Galella Collection via Getty

1987, American Music Awards

Madonna sported a more glamorous look at the 1987 American Music Awards, where she collected the award for Favorite Female Pop/Rock Video in this shimmering off-the-shoulder number.

Madonna wearing a white bodysuit cone bra
Madonna. Thierry Orban

1990, ‘Blond Ambition’ Tour

For her 1990 “Blond Ambition” world tour, Madonna personally reached out to Jean Paul Gaultier to design her iconic costumes. After she ascended the stage in a pinstripe suit, Madonna whipped off her jacket during the opening number to reveal a pink conical bra leotard. The structured corset was belted at the waist, but it still allowed enough movement for the singer to perfectly execute all of her choreography.

Madonna wearing a full gown with fan
Madonna. Getty Images

1990, MTV VMAs

Later that year, Madonna channeled Marie Antoinette when she performed “Vogue” at the MTV Video Music Awards in an elaborate costume by Marlene Stewart that was fit for Versailles.

Madonna wearing a white dress with fur throw
Madonna and Michael Jackson. Ron Galella Collection via Getty

1991, Academy Awards After Party

From her hair to her white stole, Madonna went for a full-on Marilyn Monroe moment when she attended an Oscars afterparty on the arm of Michael Jackson. She wore a custom embellished strapless gown by Bob Mackie, but it was her Harry Winston diamond earrings, necklace and bracelets (which, when combined, were worth more than $20 million) that really stole the show—diamonds are a girl’s best friend, after all.

Madonna wearing an encrusted bodysuit and black boots
Madonna. Ron Galella Collection via Getty

1991, Madonna: Truth Or Dare NYC Premiere

The New York City premiere of Madonna’s documentary marked the first time that the Queen of Pop wore Dolce & Gabbana; she arrived in a multi-colored, jeweled bustier that she paired with thigh-high stockings, an oversized black jacket and a darker hair color. D&G design duo Domenico Dolce and Stefano Gabbana would later go on to create the costumes for the singer’s 1993 “The Girlie Show” tour, and Madonna would even collaborate on a line of sunglasses with the Italian fashion house in 2010.

Madonna wearing a cone bra with pink throw
Madonna. AFP via Getty Images

1991, Cannes Film Festival

At first glance, Madonna appeared to be going a more conservative route when she arrived at the Cannes Film Festival for the premiere of her documentary, Madonna: Truth or Dare (also titled In Bed with Madonna). But beneath her pink coat, the singer revealed a lingerie set by Jean Paul Gaultier, complete with her now-signature cone bra.

Madonna wearing pale blue nightgown
Madonna. Getty Images

1995, Bedtime Story Party

To promote her new album, Bedtime Stories, Madonna threw a pajama party in New York City, where she donned a long silk nightgown under a leopard-print coat.

Madonna wearing a red feathered ensemble
Madonna. Sygma via Getty Images

1996, Evita Premiere

For the Los Angeles premiere of her 1996 film Evita, Madonna channeled on-screen leading lady Eva Perón in a red ombré Versace dress that was covered in flowers, and styled with a veiled fascinator.

Madonna wearing a black dress with matching gloves
Madonna. Ron Galella Collection via Getty

1997, Golden Globe Awards

Several months after giving birth to her first child, Madonna attended the Golden Globes (where she won Best Actress for her role in Evita) in a black Dolce & Gabbana bustier gown, which she styled with opera gloves, a diamond necklace and earrings, and a classic red lip and smoky eye combo.

Madonna in a space-themed dress and cape
Madonna. Ron Galella Collection via Getty

1997, Met Gala

Madonna’s first Met Gala was meant to celebrate the late designer Gianni Versace, and for the occasion, she wore a blue floral-print gown from the Italian fashion house, with a matching cape that was printed with astrology motifs and trimmed in fur.

Madonna in a fitted bodice with full skirted yellow gown
Madonna. Getty Images

1998, VH1 Vogue Fashion Awards

For the now-defunct VH1 Vogue Fashion Awards, Madonna wore a corseted yellow gown by the then-relatively unknown designer Olivier Theyskens. The long-sleeved gown, which featured gothic elements throughout that Madonna played up with her jet black hair, helped put Theyskens on the fashion map. 

Madonna wearing a black leather dress with ripped stripes
Madonna. Ron Galella Collection via Getty

1998, Fire & Ice Ball

In 1998, Madonna attended the star-studded Fire & Ice Ball, benefiting the UCLA Women’s Cancer Research Program, with Donatella Versace. She wore a slashed black leather Versace dress, which featured an open back and fur-trimmed skirt that was made edgier thanks to Madonna’s sleek, dark hairstyle.

Madonna in a red kimono
Madonna. Getty Images
Madonna in a white tank and lavender pants
Madonna. Ron Galella Collection via Getty

1999, Grammy Awards

In a red kimono-style number by Jean Paul Gaultier, Madonna opened the 1999 Grammys with a performance of “Nothing Really Matters” from her 1998 album, Ray of Light. Afterwards, the singer (who won three awards, including Best Pop Album) changed into a more relaxed white tank top and embellished lavender pants from the Gucci spring 1999 collection—and her red lip and eyeshadow from her onstage look were, impressively, still intact.

Madonna in a white suit
Madonna and Guy Ritchie. WireImage
Madonna with an embroidered white suit jacket
Madonna and Guy Ritchie. Getty Images

2001, Snatch Premiere

Weeks after saying “I do,” Madonna and her husband, director Guy Ritchie, attended the premiere of his latest film sporting coordinating suits. While Ritchie opted for all-black, Madonna chose a cream suit with “Mrs. Ritchie” embroidered on the back of her jacket.

Madonna wearing a fur-trimmed black coat
Guy Ritchie and Madonna. WireImage
Madonna wearing a navy dress with jewelry
Madonna and Queen Elizabeth II. Getty Images

2002, Die Another Day Premiere

The Queen of Pop met the Queen of England in 2002, at the London premiere of the James Bond film Die Another Day, for which Madonna wrote and sang the theme song. Going a more conservative route for the occasion, Madonna chose an embroidered black dress that she paired with a fur-trimmed black coat, plus a polished French twist and plenty of diamonds.

Madonna wearing a black top hat and suit
Madonna. WireImage
Madonna performing with Britney Spears and Christina Aguilera
Britney Spears, Madonna and Christina Aguilera. FilmMagic

2003, MTV VMAs

For one of the most iconic VMA performances of all time, Madonna recreated her 1984 hit, “Like a Virgin,” with the help of Britney Spears and Christina Aguilera (and later, Missy Elliott, too). This time around, Madonna played the groom in an all-black tuxedo-inspired outfit that included a belted corset top, while Spears and Aguilera put a modern spin on Madonna’s original bridal look.

Madonna wearing a bejeweled corset with black boots
Madonna. WireImage

2004, ‘Re-Invention’ Tour

Madonna played with multiple themed looks for her “Re-Invention” world tour, from Stella McCartney pinstripe suits to a circus segment in Chanel. But it was her embellished corset by Christian Lacroix—paired with fishnets and over-the-knee boots—that most embodied Madonna’s sense of style…and still somehow allowed for her to pull off backbends and headstands every night.

Madonna in a purple leotard
Madonna. FilmMagic
Madonna wearing a purple bomber and boots
Madonna. FilmMagic

2005, MTV Europe Music Awards

With a new album, Confessions on a Dance Floor, on the way, Madonna unveiled a disco-inspired take on her beloved leotard. For a performance of her latest single (which opened the 2005 MTV Europe Music Awards), the “Hung Up” singer paired her purple leotard with matching boots, a sequined belt and a feathered hairstyle.

Madonna wearing a white suit with purple shirt
Madonna. WireImage

2006, ‘Confessions’ Tour

One of the standout looks among her Jean Paul Gaultier-designed costumes for the “Confessions” world tour was this three-piece suit, which appeared to reference John Travolta’s character in the 1977 classic Saturday Night Fever.

Madonna wearing a fitted black dress with straps
Madonna. FilmMagic

2007, Vanity Fair Oscar Party

To attend the Vanity Fair Oscar party in 2007, Madonna turned to an old favorite: Dolce & Gabbana. She accessorized the strappy black satin gown with stacks of diamond bracelets and a crystal-embellished clutch.

Madonna wearing a black sheer dress with white details
Madonna. Getty Images

2008, Rock And Roll Hall Of Fame

After more than 20 years of musical contributions, Madonna was finally inducted into the Rock and Roll Hall of Fame in 2008. Her look for the evening came courtesy of Chanel’s spring 2008 collection, in the form of an entirely sheer dress with black and white sequin details.

Madonna wearing a dress of crystal ombre with black
Madonna. WireImage

2008, Cannes Film Festival

In 2008, Madonna returned to Cannes with a new documentary, this time putting the focus on Malawian orphans in I Am Because We Are. For the premiere, Madonna opted for a black Chanel couture design that was covered in sequins and accented with fringe and feathers along the sleeves and skirt.

Madonna wearing a pink dress with bow
Madonna. WireImage

2008, amfAR Cinema Against AIDS Gala

Dressed in a long-sleeved coral dress by Stella McCartney, Madonna auctioned off one of her own Chanel handbags during the Cannes amfAR gala, to benefit AIDS research.

Madonna wearing black boots with a color-accented bodysuit
Madonna. WireImage

2009, ‘Sticky & Sweet’ Tour

Madonna’s “Sticky & Sweet” world tour featured bespoke costume designs from Moschino, Miu Miu and Stella McCartney. But it was Givenchy (and then-creative director Riccardo Tisci) that created the bulk of her looks, including this black dress that was accented in multicolored ribbons and accessorized with strands of gold and hot pink necklaces (an ode to her early days, perhaps).

Madonna in a rich blue silk dress
Madonna. FilmMagic

2011, Met Gala

Rather than go the unconventional route at the 2011 Met Gala, Madonna went Old Hollywood glam in this pale blue satin Stella McCartney design. The short-sleeved gown featured an added dose of sparkle thanks to silver star embellishments that started at the bodice and ran down the entire back of the train. She wore her blonde hair styled in volumized curls, and completed the look with a red lip.

Madonna wearing a blue dress with red butterflies
Madonna. Getty Images

2011, Venice Film Festival

Madonna may have taken a behind-the-scenes role as writer and director of the 2011 film W.E., but she celebrated its premiere at the Venice Film Festival in a statement-making Vionnet gown (the French fashion house was featured in the movie, too). The pale blue number included bright red butterflies embroidered throughout, and Madonna gave it a retro feel with Old Hollywood waves, a red lip and red sunglasses.

Madonna wearing a black dress and cape with red gloves
Madonna. FilmMagic

2012, W.E. UK Premiere

For the U.K. premiere of W.E. in London, Madonna added a few twists to her black velvet Jean Paul Gaultier column gown, with a black lace cape by Dolce & Gabbana and red leather driving gloves by Chanel that matched her red lip. Van Cleef & Arpels jewelry added some sparkle, and Madonna even wore a customized ‘WE’ pendant.

Madonna wearing a grey tiered dress
Madonna. WireImage

2012, Golden Globe Awards

Madonna wore Reem Acra when she took home her second Golden Globe award (this time for Best Original Song in W.E.) in 2012. The elaborate gown featured a silver bodice that sparkled with embellishments, and a voluminous dark green skirt. Madonna paired the look with a more laidback beauty aesthetic, but upped the drama with diamond jewelry (including a cross necklace) and one leather driving glove.

Madonna wearing a gold gladiator-style outfit
Madonna. WireImage

2012, Super Bowl Halftime Show

In 2012, Madonna reached another music milestone when she headlined the Super Bowl halftime show. The “Vogue” singer once again turned to Riccardo Tisci, who designed not one, but three Givenchy looks for her performance (all of the changes taking place onstage, of course). After entering in an embellished gold cape, Madonna spent the bulk of her performance in this gladiator-inspired belted mini dress, before closing out the show in a black sequined coat.

Madonna wearing pinstripe pants and cone cage
Madonna. WireImage

2012, ‘MDNA’ Tour

Jean Paul Gaultier put a futuristic spin on Madonna’s cone bra with this cage-like version that she wore during her “MDNA” world tour, paired with pinstripe pants, a white shirt and tie and black gloves.

Madonna wearing a plaid blazer set
Madonna. Getty Images

2013, Met Gala

Madonna fully embraced the 2013 Met Gala’s punk theme in the most mini of blazers by Givenchy. The (mostly) all-black look included metallic studs and safety pins, a chain belt and fishnets, with Madonna adding a black wig to complete the ensemble.

Madonna wearing a black suit with hat and cane
David Banda and Madonna. WireImage

2014, Grammy Awards

In a sweet matching sartorial moment with her son, Madonna wore a black Ralph Lauren suit from the designer’s spring 2014 collection. The tailored look featured wide-leg pants, a cross pendant-accessorized black tie and crystal-encrusted fingerless gloves that she kept for her onstage performance, switching out suits for a white Ralph Lauren design.

Madonna wearing black lingerie style set
Madonna. WireImage

2015, Grammy Awards

A year later at the 2015 Grammy Awards, Madonna took an entirely different approach with her red carpet look, wearing a Givenchy design that was a cross between burlesque and matador (and on theme with her single, “Living For Love,” which she performed later that evening). The totally out-there look included lace and embellished detailing, leather gloves, over-the-knee boots and a veiled hat.

Madonna wearing a printed black dress with cape and gloves
Madonna. FilmMagic

2015, Met Gala

Madonna donned custom Moschino for the 2015 Met Gala, in an off-the-shoulder black gown complete with gloves, cape and graffiti that read ‘Rebel Heart’—a nod to the singer’s most recent album (and upcoming tour) of the same name.

Madonna wearing a feathered crystal-dripping outfit
Madonna. Kevin Mazur

‘Rebel Heart’ Tour

Madonna’s “Rebel Heart’ marked her 10th tour, and it featured an array of elaborate themed costumes, from a matador-inspired number by Fausto Puglisi to a colorful look by Gucci. But it was the glittering, flapper-esque design by Moschino’s then-creative director Jeremy Scott that was perhaps the most noteworthy, with its Swarovski crystal-embellished fringe.

Madonna wearing an embroidered suit
Madonna. Penske Media via Getty Images

2016, Billboard Women In Music

To celebrate being named Billboard’s Woman of the Year in 2016, Madonna turned to Gucci’s then-creative director Alessandro Michele for a custom look. Landing on a suit that was embroidered throughout with flowers and tigers, it was the back of the jacket that made the biggest statement, as it featured Greek embroidery that read “the goddess of music who brings joy,” according to stylist Arianne Phillips.

Madonna wearing a black gown with braids
Madonna. Getty Images
Madonna wearing a white gown with flowing sleeves
Madonna. Getty Images for The Met Museum/

2018, Met Gala

The 2018 Met Gala’s “Heavenly Bodies” theme seemed made for Madonna, whose music and fashion have often drawn from her own upbringing in the Catholic church. The “Like a Prayer” singer teamed up with Jean Paul Gaultier on this black gown, which featured a cross on the bodice and was accessorized with a black veil and bejeweled headpiece. Inside the Met, Madonna changed into a white gown (complete with her go-to Jean Paul Gaultier corset) for a short performance.

Madonna wearing a black tight outfit with military hat
Madonna. Getty Images for MTV/ViacomCBS

2021, MTV VMAs

At the 2021 VMAs, MTV celebrated 40 years since its 1981 debut (though the first televised VMAs didn’t come until 1984), and Madonna kicked off the evening’s festivities with a look that certainly garnered attention. Underneath a Burberry trench coat, Madonna revealed a custom latex corset by House of Harlot that was styled with a matching hat, gloves and fishnet stockings.

Madonna wearing a full black suit with skirt
Madonna. Getty Images for The Recording A

2023, Grammy Awards

Madonna and her new stylist Rita Melssen turned to the Mugler archives for the singer’s appearance at the 2023 Grammy Awards. The black-and-white ensemble was from Mugler’s 1997 couture collection, and was styled with black fishnet stockings and sky-high platforms by Vivienne Westwood.

Madonna’s Most Iconic Fashion Moments





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