From her 4-decades-long pop music career
In a silk, embroidered, Stella McCartney gown that was elegant but ultimately underwhelming.
Photo: Kevin Mazur/WireImage
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.
was sporty, but not as daring as other signature looks.
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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.
to the 1992 launch for her book, "S*x."
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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 "S?x," the book sold 150,000 copies the first day, according to Newsweek.
consisted of a grey tutu paired with a blazer.
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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.
And Madonna's kimono-inspired look from the Grammy Awards, in 1999, is a prime example.
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Was 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.
Madonna has always pushed the envelope, but sometimes she may go too far.
by wearing this vampy, yellow corseted gown.
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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.
to Vanity Fair's Academy Awards afterparty in 2006.
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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."
including for Madonna's 1991 Oscar's afterparty look.
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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.
look blended punk and fairytale wedding perfectly.
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Who thought wedding dresses could be punk? Madonna, that's who.