Madonna’s Best Fashion Moments of All Time

Gold-en Girl

Just five years after she left the University of Michigan to become a dancer in New York City, Madonna Louise Ciccone made her first move as a worldwide trendsetter — stacking her black rubber bracelets and flashing her crop top for TV’s Solid Gold while performing “Holiday” in 1983.

Bow Tied

Madonna played it sweet and tough (check out that black leather!) as she starred as a street dancer turned fashion model in the video for 1984’s “Borderline.”

Fun fact: Besides one very big bow, the clip also starred a then-unknown John Leguizamo as one of the singer’s pals.

“Virgin” Territory

After Madonna — clad in a tulle skirt, garters, a white bustier and a “Boy Toy” belt buckle — writhed her way through the 1984 MTV Video Music Awards, underwear was suddenly the new outerwear.

“It’s not like I was saying, ‘Don’t pay attention to the clothes — to the lingerie — I’m wearing,’ ” she told Rolling Stone in September 1987. “Actually, the fact that I was wearing those clothes was meant to drive home the point that you can be sexy and strong at the same time. In a way, it was necessary to wear the clothes.”

Big Screen Ambition

The movie was Desperately Seeking Susan, but after Madonna made her screen debut in the 1985 caper as a “free-spirited, adventurous femme fatale,” it was her gilded jacket that was in demand.

Diamond Girl

Paying homage to Marilyn Monroe‘s performance of “Diamonds Are a Girl’s Best Friend” (from 1953’s Gentlemen Prefer Blondes), Madonna charmed suitors and picked up baubles in a slinky pink satin gown in the 1985 video for “Material Girl.”

Although it wouldn’t be the last time she echoed Monroe, the pop star later said to Smash Hits magazine, “I don’t think I’m like Marilyn Monroe in a lot of ways. The main thing that we have in common is that we bleach our hair.”

Jacket Required

Booties? Check. Lace leggings? Check. Miniskirt? Check. Madonna showed off her signature look during “Dress You Up,” the opening number for her first U.S. outing, 1985’s Virgin Tour.

Preacher Girl

Only Madonna could shock with a make-under. The singer embraced her inner school marm in the 1986 video for “Live to Tell,” a song she wrote for then-husband Sean Penn‘s film At Close Range. Although the movie flopped, the single topped Billboard‘s Hot 100 chart.

Couple Outing

In what would become a familiar sight, a dour-looking Penn escorted Madonna — who mixed it up with an evening gown and a leather jacket — to the premiere of At Close Range.

The couple’s nearly four-year marriage (they divorced in 1989) would become known for public spats and paparazzi standoffs. “I do believe we all have soulmates,” Madonna told PEOPLE. “I don’t believe that we necessarily end up with them.”

Daddy’s Girl

Winking at her Italian roots, Madonna boasted that “Italians Do It Better” in the controversial 1986 video for “Papa Don’t Preach,” which told the story of an unwed pregnant girl who decides to keep her baby.

The video was also a star-making turn for Do the Right Thing actor Danny Aiello, who told PEOPLE the casting put him “on my way.”

Tassel Hassle

Another day, another controversy! In the 1986 clip for “Open Your Heart,” Madonna played an exotic dancer — tassels, fishnets and all — who befriends a minor after he sneaks into her strip club.

Although groups protested the use of the youth, Madonna later described the music video as a statement about innocence.

Island Beauty

Madonna’s flirtation with the Spanish language and Latin culture began with the bilingual hit “La Isla Bonita.” In the 1987 video, the newly brunette singer dances in a red ruffled flamenco dress to the sounds of guitar.

That Girl

In the 1987 crime romp Who’s That Girl, Madonna played a spunky but ditzy ex-con named Nikki wearing — what else? — a leather jacket, fingerless gloves and a miniskirt.

“There was just something about the character — the contrasts in her nature, how she was tough on one side and vulnerable on the other — that I thought I could take and make my own,” she told Rolling Stone that same year.

Platinum Hit

To accept an American Music Award in 1987, Madonna paired her then-signature blonde bob with a matching ivory-colored off-the-shoulder dress, dark brown eyebrows and a bright red lip.

Church Lady

A steamy embrace with a saint, a burning cross and a loose shoulder strap would all add up to one of the pop singer’s biggest media storms. After the debut of “Like a Prayer” on March 3, 1989, the Vatican banned her from performing in Italy and Pepsi dropped her from its ad campaign — but Madonna kept her reported $5 million fee.

Good Jeans

In matching painted denim cutoffs and jeweled bras, Madonna and then-pal comedian Sandra Bernhard performed a raunchy rendition of the Sonny & Cher classic “I Got You Babe” at an AIDS benefit in 1989.

New Expression

As the ’80s drew to a close, Madonna — fresh from filing for divorce from Penn — ditched her feminine style and debuted a bold, androgynous look. Standing tall in menswear and brandishing a monocle, the singer flexed her muscles (literally), flashed her bra and seduced a sweaty factory worker in the epic video for “Express Yourself.”

Surfer Girl

A softer side of the singer emerged from the surf in the video for “Cherish,” Madonna’s surprisingly sweet 1989 love song. Directed by famed photographer Herb Ritts, Madonna — in a clingy black shirtdress — frolicked in the water and flirted with mermen.

In Vogue

Taking the dance sensation out of New York’s gay underground and on the road, the singer vogued her way around the world on her 1990 Blond Ambition Tour in her iconic Jean Paul Gaultier cone bra.

Midas Touch

As documented in the 1991 behind-the-scenes film Truth or Dare, the Blond Ambition tour sparked protests from the Vatican to Canada. Among the show’s controversial elements: her performance of “Like a Virgin,” during which the singer simulated masturbation while wearing a gold cone-topped corset.

Show Pony

Her sky-high, glamorous ponytail gave this satin cone-bra look an almost-sporty vibe during her Blond Ambition tour.

Going Dotty

Gaultier designed the costumes for Blond Ambition, including this polka-dot getup for one of the tour’s frothiest numbers, a booty-bumping version of Madonna’s early hit “Holiday.”

French Dip

Channeling the look of Marie Antoinette’s court at Versailles, Madonna thrilled the crowd at the 1990 MTV Video Music Awards with a lush, naughty performance of “Vogue.” Although the video snagged best direction, it lost video of the year (to Sinead O’Connor‘s “Nothing Compares 2 U”).

She’s Breathless

Madonna was sleek and sexy as ’50s-era nightclub siren Breathless Mahoney in the 1990 live-action comic-book flick Dick Tracy. Although the film wasn’t a hit, I’m Breathless, Madonna’s album of songs from and inspired by the movie, eventually went double-platinum, thanks to hits like “Vogue” and “Hanky Panky.”

Tracy Twosome

After gossip spread that Madonna was hooking up with her Dick Tracy costar, legendary playboy Warren Beatty, the twosome stepped out, hand-in-hand, at the film’s Washington, D.C., premiere in 1990.

But Madonna stole the spotlight — sporting flowers in her hair, chunky shoes and a babydoll dress, long before Courtney Love would pair the look with grunge.

Odd Couple

She may have been dripping in $20 million Harry Winston diamonds, but neither her bling nor her daringly low-cut Bob Mackie gown had people talking at the 1991 Academy Awards.

Madonna arrived with Michael Jackson, and whispered and giggled in his ear at the post-show bash at Spago. But it was all just for show, with Madonna soon ditching the King of Pop for beau Beatty.

Cannes Do

In a Gaultier cone bra and miniskirt (similar to the black ones he had designed for her Blond Ambition tour), a brunette Madonna made a grand entrance at the 1991 Cannes Film Festival for the premiere of Truth or Dare.

Play Ball

There may be no crying in baseball, but there sure are short skirts! In the 1992 hit A League of Their Own, Madonna starred as “All the Way Mae” Mordabito, a center-fielder for the Rockford Peaches during WWII. The film also starred Tom Hanks, Geena Davis and Rosie O’Donnell, who became a close pal of the pop star.

Breast in Show

Madonna got something off her chest — her top! — at Gaultier’s fall runway show in 1992. The topless singer joined fellow stars like Billy Idol and Faye Dunaway at the charity event, which raised $750,000 — along with eyebrows — for amfAR (the American Foundation for AIDS Research).

Très Sheep

Dressed as a vampy version of Little Bo Peep — down to the stuffed toy lamb in her arms — Madonna arrived at the Oct. 15, 1992, release party for her scandalous coffee-table book, Sex.

The bash, held in New York’s then-seedy Meatpacking District, featured models acting out fetish fantasies with whips and handcuffs, and some just reclining in tubs filled with caramel corn.

Show Girl

Touring in support of her sexually charged album Erotica, a leather-clad Madonna presented The Girlie Show, a naughty burlesque-themed tour that featured topless dancers, clowns and a simulated orgy during “Deeper and Deeper.” One of her featured dancers included Dancing with the Stars judge Carrie Ann Inaba, who performed topless.

Nothing but Net

Going back to her love affair with Spanish culture, Madonna played the part of a woman obsessed with a bullfighter in the 1994 video for “Take a Bow.”

The ballad, from her album Bedtime Stories, was Madonna’s longest-running No. 1 hit, topping the charts for seven weeks. The romantic and retro video — part of her campaign to win the film role of Evita — was a marked departure from the singer’s Erotica-era sexualized persona.

“Nature” Girl

Madonna returned to sexual imagery with the 1995 video for “Human Nature,” a tongue-in-cheek look at bondage that acted as a response to critics of her Sex book.

Squeezed into a latex bodysuit and wearing cornrows, Madonna alternately wields a whip, is bound to a chair and poses with a Chihuahua — in matching latex.

First Lady

The singer went ’40s glam in elegant suits and hats as beloved Argentinean presidential wife Eva Péron in the 1996 musical film Evita.

During filming, Madonna discovered she was pregnant with daughter Lourdes. “It got hard toward the end, just in terms of working long hours and being on my feet,” Madonna said. “But it was okay, I got through it.”

A Winner at Last

The pop star flaunted her curves in a plunging Dolce & Gabbana bustier gown at the 1997 Golden Globes, where she won best performance by an actress in a motion picture — musical or comedy for Evita. After the show, Madonna mentioned her real lucky charm: daughter Lourdes, born on Oct. 14, 1996. “She brings me the most luck,” the singer said backstage.

Seeing the ‘Light’

The new mom — and new devotee of Kabbalah — played it simple in a denim jacket, softly waved hair and now-omnipresent red-string bracelet in the video for “Ray of Light,” the lead single off the like-titled 1998 album.

“It’s really great,” she told Kurt Loder about her newfound religion. “The whole idea of cause and effect, for every action there’s a reaction: It’s like, you pull in what you put out, basically. If you want to have goodness in your life, you have to give it.”

Inspired by Japanese Fashion

Madonna embraced the East Asian style for her show-opening version of “Nothing Really Matters” at the 1999 Grammy Awards in L.A., where she finally won. Accepting the Grammy for best pop album in her red Gaultier kimono, the toned-down singer thanked her co-producers and co-writers.

American Girl

For the 2000 movie The Next Best Thing, which starred Madonna and Rupert Everett, the singer recorded a cover of Don McLean’s classic “American Pie.” The remake would become her first single of the new millennium. The video had a simple concept: an all-American Madonna dancing around with a U.S. flag in blue jeans and a tiara.

Material Mom

Two years after welcoming Lourdes, Madonna — who had tamed her wild side with motherhood — was pregnant again in May 2000. This time, she was expecting son Rocco, born Aug. 11, with movie director Guy Ritchie.

“Music” Maker

From earth mother to rhinestone cowgirl: “Music,” the first single from her new album by the same name, had the then-pregnant singer back in the clubs — at least in her video — in a white fur coat and a wide-brimmed hat.

Fun fact: The gold limo that shuttled Madonna and her friends in the 2000 clip was driven by actor and comedian Sacha Baron Cohen, then virtually unknown in the U.S.

Cowgirl Boogie

Madonna — in Dsquared leather cowboy shirts — took her Western inspiration and kicked it up in the video for her next single, “Don’t Tell Me,” which featured plenty of boot-scootin’ and line dancing.

In the Trenches

The year 2000 brought a stint of strawberry blonde hair and this black leather trench coat, which she wore on MTV’s TRL.

Mrs. Ritchie

At the January 2001 premiere of Ritchie’s Snatch, Madonna splashed her new name across her back: Mrs. Ritchie. The singer married the director at the Great Hall of Scotland’s 19th-century Skibo Castle on Dec. 22 in a Stella McCartney-designed dress. A 4-year-old Lourdes was a flower girl, and Rocco sat with a nanny in the front row.

Lucky Girl

Before embarking on her 2001 Drowned World Tour — her first since 1993 — Madonna performed a show at New York’s Roseland Ballroom in a T-shirt giving a nod to another chart-topping lady.

“Britney Spears became my talisman for the week,” Madonna told Elle in 2001. “I became obsessed with wearing [Britney] T-shirts. I slept in them, as well. It was like I felt it would bring me luck. And it did.”

Rocker Chick

When the Drowned World Tour kicked off in September 2001, the club girl proved herself a rock star, coming out in punk-inspired costumes and bearing her own six-string.

“I kept saying to myself, ‘What am I f—— doing? Who am I kidding? I just learned how to play guitar! Why am I doing this?’ ” Madonna said at the time.

The Kiss Seen ‘Round the World

Paying homage to Madonna’s classic 2003 VMA performance of “Like a Virgin,” the “Baby One More Time” singer and Christina Aguilera gave the hit a whirl before the icon herself made a grand entrance. In a military-inspired outfit — the theme of her American Life album — Madonna sang her new single “Hollywood” before locking lips with both popsters.

Wild “English Rose”

Looking more “Live to Tell” than “Like a Virgin,” Madonna covered up in a conservative Prada floral frock for the launch of her children’s book, The English Roses, in September 2003. The new author sat on a swing at London’s Kensington Roof Gardens between children Lourdes, then 6, and Rocco, then 3, and read passages from the book, about school friends who are jealous of another girl.

Shirt Tales

Winking at the “Italians Do It Better” shirt she wore in the “Papa Don’t Preach” video, Madonna proudly proclaimed that “Kabbalists Do It Better” during the finale of her 2004 Re-Invention Tour.

Nun of That

Madonna outraged Catholic leaders yet again when she and husband Ritchie dressed up as a nun and the Pope for a London costume party celebrating the Jewish holiday of Purim in March 2005. Madonna’s rep Liz Rosenberg said, “They meant no disrespect at all.”

Disco Queen

Sporting a purple leotard similar to her cover outfit on her 10th studio disc, Confessions on a Dance Floor, Madonna promoted the ’70s-inspired dance album at G-A-Y — a weekly party at London club Astoria — in November 2005.

Getting Her Point Across

The singer’s decision to perform “Live to Tell” while mock-crucified was — not surprisingly — the most controversial element of her 2006 Confessions Tour. After the Vatican condemned her as blasphemous, the singer issued a press statement, saying, “My performance is neither anti-Christian, sacrilegious or blasphemous. Rather, it is my plea to the audience to encourage mankind to help one another and to see the world as a unified whole.”

She added, “I believe in my heart that if Jesus were alive today, he would be doing the same thing.”

On the Right Track

The yoga aficionado and dedicated gymgoer modeled samples from her eponymous clothing line for H&M in the streets of London. The singer — wearing the white tracksuit she sported in advertisements for the line — offered trench coats, other tracksuits, sleek dresses and more for affordable prices.

A Moving Moment

Chic in Chanel haute couture, Madonna premiered her documentary I Am Because We Are, about orphans in Malawi, at the Cannes Film Festival in May 2008. The work was inspired by her own experience of adopting a Malawian boy, David Banda.

“This is a film I want the world to see,” a choked-up Madonna told the audience.

A True Fighter

A champion tough to beat both on and off the stage, Madonna suited up as a heavyweight boxer in press photos for Hard Candy, her 11th studio album, which was released 25 years after that first Solid Gold appearance.

Dare to Bare

Madonna — and her backside — made an appearance at the 2016 Met Gala, dressed in a strappy black Givenchy thong bodysuit with front cut-outs, a sheer lace dress and thigh-high leather boots.

Woman in Black

A ’50s-inspired blowout, dramatic black sunglasses, a graphic T-shirt, a hint of lace and a lot of studs: the Madonna starter pack, which she wore on a 2017 episode of The Tonight Show Starring Jimmy Fallon.

All That Glitters

In one of the most iconic Super Bowl performances of all time, the star took the stage in 2012 wearing a dazzling gold dress and a dramatic headpiece to perform a medley of her hits.

French Connection

Paired with an oversized beret, Madonna attended the 57th annual Grammy Awards in 2015 wearing an ensemble of lace, thigh-high boots and, of course, a mesh veil.

Pretty in Pink

Though she may be committed to wearing all black all the time, Madonna did change things up for this 2017 selfie, in which she not only wore a pink top but also a matching shade of eye shadow.

Shine Bright

To celebrate the launch of her skincare line, MDNA Skin, Madonna channeled the King of Pop in a black sequin-embellished jumpsuit, oversized black sunglasses and her signature structured waves.

Cross the Line

To no surprise, the singer stuck to the “Heavenly Bodies: Fashion and the Catholic Imagination” theme at the 2018 Met Gala. Madonna wore a long-sleeved, billowing Gaultier gown with sheer-paneled cross detailing, which she paired with a crystal-accented crown, a black veil and a ton of cross-inspired jewelry.

Blushing Queen

A selfie showed the Queen of Pop donning a baby pink sheer shirt with textured undergarments underneath. Madge paired the look with a dark blush pink lipstick.

Miss Madame X to You

In 2019, Madge sported a ruffled, polka-dot number with her signature eyepatch that was synonymous with her Madame X era.

All Hail

At the 2019 Eurovision Song Contest, she sported a metallic corset, a shiny crown and black knee-highs — in true queen fashion.

What’s Grillin’?

On an August 2022 episode of The Tonight Show, Madonna revealed her present to herself. “They’re my ‘birthday grills,'” she explained. “It’s almost my [64th] birthday, so I got myself a pair of grills.”

She continued, “I just like the way it looks — it’s mouth jewelry — and I have really ugly teeth.”

Madonna at 65

Teasing her Celebration World Tour on Instagram, Madonna also teased a futuristic new look, wrap-around shades and all!