No one does a pop era like Madonna. Since kickstarting her career in the early 80s, the star has switched up her look so frequently — and so drastically — it can be hard for even her most dedicated fans to keep up. Back in the 80s, the singer popularised the concept of the pop “era”, continuously reinventing her image with each album cycle. For “Like a Virgin”, Madonna became the not-so-virginal bride, wedding dress and all. “Material Girl” saw the singer channel Marilyn Monroe’s bombshell energy. And with “Like a Prayer”, she transformed into the penitent sinner in a cross necklace and black slip dress. In the decades since, the singer has passed through near-innumerable style phases: Blond Ambition’s cabaret chic, Erotica’s dominatrix, Music’s folktronica cowgirl and the jazzercise-core of “Hung Up”, just to name a few.
Madge and her chameleonic tendencies laid the blueprint for modern popstardom. And her ability to switch it up has also captured the public and the media’s attention for more than 40 years. As Madge kicks off her twelfth (!) concert tour, we look back at the star’s most stylish, most shocking, and most iconic outfits of all time.
Subscribe to i-D NEWSFLASH. A weekly newsletter delivered to your inbox on Fridays.
At the MTV VMAs, 1984
On the cover of 1984’s Like a Virgin, Madonna wears a white wedding dress. An appropriately “virginal” look, suited to the album title. Or is it? Upon closer inspection, the look isn’t as chaste as its namesake would suggest. Made up of a racy lace bodice and cheeky “Boy Toy”-emblazoned belt, Madonna’s Like a Virgin ensemble positioned the popstar as not just an object of desire, but as a sexually-liberated subject — the desirer, herself.
Here, Madge wears the outfit to the year’s MTV VMAs, where she gave a writhing, panty-flashing rendition of the album’s titular single. The boundary-pushing performance cemented Madge’s reputation as a pop provocateur and style icon. As Arianne Phillips, the singer’s longtime personal stylist, put it: “[the 1984 VMA’s performance was] one of the most shocking, liberating and influential moments in pop culture/fashion history. Fashion has never been the same.”
“Like a Prayer” music video, 1989
Anyone who thought Madge was finished courting controversy after Like a Virgin was sorely mistaken. In fact, the singer only upped the ante with the release of 1989’s Like a Prayer and its titular lead single.
As intended, the “Like a Prayer” music video was more provocative than anything Madonna had done before, broaching the topics of racism, religion and female sexuality in one fell swoop. From a narrative perspective, the video tells the story of a Black man falsely accused of murdering a white woman, and the protagonist’s (played by Madonna) struggle to come forward as a witness. Thematically, the clip compares religious with sexual ecstasy, and is rife with such imagery: Madonna is branded with the stigmata, kisses a black saint and dances in front of a series of burning crosses. To help Madonna achieve the video’s penitent sinner look, her costume designer dressed the singer in a cross necklace and a black slip dress previously owned by 50s star (and sex symbol) Natalie Wood.
At the MTV VMAs, 1990
In 1990, Madonna returned to the VMAs to court more controversy… in royal court attire. That’s right: the star donned a full pannier gown and powdered wig to deliver an ultra-campy, bacchanalian rendition of her hit single, “Vogue.”
“We know historically that the French were the biggest posers and [the song is about] voguing and posing,” costume designer Marlene Stewart said of the Marie-Antoinette-inspired look. “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 song pays homage to New York’s voguing scene and, incidentally, many of the performance’s “courtiers” were OG Voguers.
On the Blond Ambition tour, 1990
This is it: Madonna’s most infamous look. On the first night of her 1990 Blond Ambition tour, the singer ripped open the blazer of her zoot suit to reveal a cone-breasted satin corset — you know the one. The iconic cone bra was created by fashion enfant terrible Jean Paul Gaultier, who drew inspiration from the pointy “bullet” bras worn by 1940s film stars. As its namesake suggests, the look was assertive and intimidating, weaponising the female form by transforming its curves into spikes that seemed to prick. It was an outfit for a woman in complete control of her sexuality: wearing the JPG corset (over a pair of pants, no less) Madge thrusted her hips and touched herself as she sang, “You’ve got to make him express himself”.
At Cannes Film Festival, 1991
When it comes to fashion, Madonna tends to partner with only the industry’s most provocative names. As the saying goes: real recognizes real. Throughout her career, Madge has collaborated with the likes of Jean Paul Gaultier (who outfitted the Blond Ambition tour) and Steven Meisel (who photographed the Like a Virgin cover and the singer’s 1992 book Sex).
Madonna’s longest-spanning fashion industry partnerships, however, is with British designer Vivienne Westwood. The duo’s relationship dates back to the beginning of Madge’s career, when the singer wore a look from the designer’s 1983 “Witches” collection in the “Borderline” video. Since then, Madonna has worn a number of Vivienne’s designs on screen and on stage. Among them is the corset she wore in 1993’s “Fever” video and this skirt suit, which she wore on the Cannes red carpet.
At the MTV VMAs, 1995
Is it any surprise that Madonna would team up with fashion’s “King of Sex”? In 1995, the singer scooped a VMA for Best Female Video wearing a look designed by Tom Ford for Gucci. The sexy satin ensemble was pulled from the house’s AW95 runway, where it had been modeled by Kate Moss and Shalom Harlow.
“Hung Up” music video, 2005
Before balletcore there was Madonna’s jazzercise-core. According to the singer, the dance-centric music video for disco single “Hung Up” was a tribute to actor John Travolta, its choreography drawing inspiration from some of the actor’s most famous films, including Saturday Night Fever, Grease and Perfect. To pay proper homage to these vintage flicks, costume designer Arianne Phillips dressed Madge in authentic 70s and 80s-era dancewear, while hairstylist Andy LeCompte fixed the singer’s locks into a Fawcett-style flip.
In the video’s most iconic sequence, Madge dances around London’s Pineapple Dance Studios wearing a hot pink wrap over a leotard and sequin dance belt, all sourced from LA vintage boutique The Way We Wore. The sequence took three hours to film — and the singer did it all with a set of broken ribs. Talk about dedication! But we wouldn’t expect anything less from the Queen of Pop.