The Transformation Of Madonna From 25 To 60

With her chic punk-inspired style, tousled peroxide blonde hair with dark roots, and defiantly confident sexuality, Madonna didn't enter the music industry quietly when she dropped her first album in 1983. Her debut singles "Everybody" and "Burning Up" both peaked at respectable number three slots on the Billboard Hot Dance Club Songs chart, and it was clear that a new and exciting superstar had announced herself. 

Speaking to Spin in 1985, the formative queen of pop shared a range of eclectic influences including Marilyn Monroe, Brigitte Bardot, and Nancy Sinatra — for the "go-go boots, miniskirt, blonde hair, fake eyelashes." It was also evident that her new lifestyle had an impact on her sound and fashion too, the magazine that as a result of her circumstances she "most identified" with Audrey Hepburn's "Breakfast at Tiffany's" protagonist Holly Golightly. "When I first came to New York, I was lonely, lived by myself," she said, "[I] was going to parties and not fitting in."

Golightly's sense of street chic — glamour on a shoestring — can be seen in Madonna's passion for invention during this era. But it can also be attributed to the kinetic art scene she was embroiled within. When her first album was being made she was dating the brilliant Jean-Michel Basquiat (via Artnet), and was rubbing shoulders with others like Keith Haring and Andy Warhol. "We all fed off each other's energy," she recalled to Vice, "and we were all inspired by each other and jealous of each other."

With "True Blue," Madonna continued to explore her sexuality alongside the traditions of her Catholic upbringing with a softer approach. She also seemed eager to offer a more romantic, naive sound which delved into the pains of growing up: Gone were the rumpled sex-hair looks of her first two albums, and in their place was a blonde crop which felt as youthful as it did modest.

Just a year earlier, Madonna told Spin that though she wanted to look like a blonde bombshell "like Brigitte Bardot" that she also wanted "to look like Jean Seberg in 'Joan of Arc'" — who iconically wore a similarly cropped blonde look to depict the Catholic martyr. She explained that her upbringing played a major part in that. "I was religious, in a passionate, adolescent way," she said, "Jesus Christ was like a movie star, my favorite idol of all."

While "Like a Virgin" wryly celebrated the joys of breaking chastity, "Papa Don't Preach" delved into the subject of teenage pregnancy. In classic Madonna style, the song attracted criticism for what some groups perceived as promoting premarital sex and premarital motherhood. Speaking to The New York Times, Madonna said it was inevitable that people would take the song the wrong way, but she was having none of it. "It's a celebration of life," she explained. "It says, 'I love you, father, and I love this man and this child that is growing inside me.'"

Madonna first dabbled with the power pairing of feminine corsetry with masculine tailoring in the David Fincher-directed video for "Express Yourself." But for 1990's "The Blond Ambition Tour," she really upped the ante when she collaborated with Jean Paul Gaultier on what would become one of her most defining and influential looks: the cone bra and pinstripe suit. 

As Vogue once described the look, this new imagining of the corset reshaped the "soft curves" of female anatomy to become "a spiky, phallic weapon" full of dominance. It made a statement, to say the least. And it was the perfect ensemble to accompany a live show that Catholic organizations threatened to ban Madonna from Italy, accusing it of "overflowing with vulgarity and blasphemy," per the Los Angeles Times.

The salacious stage show had caused a lot of pearl clutching, including an incident in Canada where she almost got arrested for pantomiming masturbation on stage, per Billboard. But this was a woman who once insisted to The New York Times that "art should be controversial," and she wouldn't have her self-expression muted for anyone or anything. "My show is not a conventional rock concert but a theatrical presentation of my music," she told reporters. "It poses questions, provokes thought and takes you on an emotional journey. ... I do not endorse a way of life but describe one."

Once she'd discovered that she'd hit a certain cultural nerve, Madonna continued to delight in digging her nails in with her most provocative works yet. The star achieved a double whammy of sexual incitement with the release of album "Erotica," and "Sex" — her book of photography which served up softcore pornography through a post-feminist lens. In both "Sex" and "Erotica" Madonna explored the outer reaches of human sexuality via a dominatrix alter ego named Dita.

As Billboard once wrote of "Erotica," the album set "the blueprint" for singers to "get raw while eschewing exploitation" and with both works she wasn't just challenging the male gaze, but "making the world her sub." Sadly, not everyone agreed and both were met with backlash. For The Guardian, Martin Amis called "Sex" "the desperate confection of an ageing scandal-addict" while Spin called the book "a con job" for teasing titillation whilst serving up "pretentious" art. But perhaps arousal wasn't the point? Madonna told the magazine that she was trying to make a simple point: "Why should we feel ashamed of our sexuality?"

Unsurprisingly, Madonna's sense of style became even more stripped-down during this period, and especially so for "The Girlie Show Tour" which followed. Her "Joan of Arc" cropped hair made a return which called to mind the idea of being burned at the stake. 

By 1996, Madonna had left behind the chaste performance and femme fury of "Bedtime Stories" to delve back into her cosplay closet. This time, however, she wasn't mimicking Marilyn Monroe but Eva Perón, the legendary political figure and former first lady of Argentina. 

Madonna had already nabbed a few credits before she scored the titular role in the musical drama "Evita." She'd gained desperately mixed reviews from starring in a slew of movies including "Desperately Seeking Susan," "Body of Evidence," "Dick Tracy," and "A League of Their Own." The latter of which caused legendary actor Debra Winger to quit when Madonna was cast. Of the music superstar's onscreen skills, she sniped to The Telegraph, "I think her acting career has spoken for itself." Regardless, Madonna was determined to be taken seriously as an actor, and "Evita" was her vehicle to do so.

Madge had "always insisted" she was the best choice for the role, and she told Roger Ebert that she "was possessed" by Perón during filming. When trying to convince the Argentine president to allow them to film in iconic political locations for the film, Madonna said she "went in costume to the meeting." She also maintained this look for most red carpet appearances that followed. She was no longer Madonna, the renegade pop star — she was Madonna, the first lady of Hollywood. 

Madonna met "Lock Stock and Two Smoking Barrels" filmmaker Guy Ritchie in 1999 and the two promptly fell in love and had gotten married and welcomed their first child together just a year later (via The Mirror). The queen of pop left the US for Britain to be with her new fella, and the distance from her home country allowed her to develop a new ironic sense of style which felt parodic of herself and of American culture. 

"Music," her eighth studio album, played around with this idea. And though it was riffing on pre-existing musical tropes, the album's genre-jumping electronica was firmly looking forward with Madonna once describing it as "the future as sound" (via Digital Spy). For the primary promotion of "Music" Madonna wore an endless supply of glitzy cowboy clobber which celebrated American identity with a garish sense of wit.

Her tongue-in-cheek ironic style experiments continued on the red carpet with her new hubby. Ritchie and Madonna would delight in wearing matching his-and-hers ensembles which often made the two look like a pair of superstar, Vegas newlyweds. Be it the "Snatch" and "Music" t-shirts they wore promoting each other's respective new releases, or the diamanté "Mrs Ritchie" encrusted bridal suit Madonna wore to the "Snatch" premiere (via Go Fug Yourself), the lovebirds toyed with the tastefulness of self-promotion and pushed it new, joyfully tacky extremes.  

Next, Madonna swapped out the military fatigues for leotards and fishnet tights. New York City's former dancing queen was back in a big way, and with 2005's "Confessions of a Dance Floor" she just wanted to spread some joy. Stating that she was "very agitated" by global events when she wrote "American Life," she told MTV that she wanted "to feel buoyant" and make something she could dance to. "I want to give other people the same feeling," she said, "There's a lot of madness in the world around us, and I want people to be happy."

The result was an album that gleefully reminded listeners of the safety and jubilance of the dance floor: Even if the world is terrible, you can always dissolve your worries into disco. It was a sound and look which worked for the star, who continued to find solace in the liberating dance vibes of her youth for her next album "Hard Candy." 

For the 2008 release, Madonna collaborated with, as Pitchfork wrote, "American men [who'd] come to define global pop." She teamed up with the Neptunes, Kanye West, and Justin Timberlake, giving her sound a polished, contemporary sound. But she also never let her collaborators forget she was the champ, and for "Hard Candy" her dance ensemble had confidently morphed into a slick boxing leotard, complete with a championship belt, presenting a proud feminine toughness: The sweetness of dance, and also the fortitude of it.

After boldly stepping back into her public persona with "Rebel Heart," Madonna decided to don an eyepatch and go undercover in her own career with the release of 2019's "Madame X." In signature Madge style, the album, which came out just before her 61st birthday, was personal and fictional all at once, with the star developing an alter-ego that she could slip into while exploring ideas close to heart. 

Speaking to "Today," Madonna described Madame X as being a global "secret agent" who "changes her identity" often. The character was inspired by the nickname her former dance teacher gave her due to her mysterious, impenetrable nature — "she could never 'identify' who Madonna was" – - a problem that the star similarly had with herself while recording. "I felt the same way," she said, "I had to create a story that was sort of the beginning of Madame X's journey."

Aesthetically, Madonna took the "greatest hits" element of her "Rebel Heart" look and intensified it within the lens of a narrative. Madame X wasn't Madonna, but an extension of her; in the album's teaser trailer, she described the character as "a dancer, a professor, a head of state ... a mother, a child, a teacher, a nun, a singer, a saint, a whore." She subsequently bound between cowboy hats and tailored suits, bridal gowns and silk floral dresses. All looks that had come to signify Madonna over the years, which were now decontextualized within a new narrative — and, as ever, blurring the boundaries between reality and performance.