Ranking Madonna's most standout looks



1/10 ● Insider
tap to see next page

In 2011, Madonna attended the Met Gala

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.

The Queen of Pop's outfit for the European Music Awards in 2005

was sporty, but not as daring as other signature looks.



Photo: Toni Anne Barson/WireImage.

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.

Madonna wore a revealing version of a traditional German dirndl dress

to the 1992 launch for her book, "S*x."



Photo: Kevin Mazur Archive/WireImage.

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.

One of Madonna's 1991 Cannes Film Festival outfits

consisted of a grey tutu paired with a blazer.



Photo: ARNAL/GARCIA/PICOT/Gamma-Rapho via Getty Images.

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.

Not all iconic looks are memorable for the right reasons,

And Madonna's kimono-inspired look from the Grammy Awards, in 1999, is a prime example.



Photo: Ron Wolfson/Getty Images.

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.

Madonna brought the drama to the 1998 VH1 Vogue Fashion Awards

by wearing this vampy, yellow corseted gown.



Photo: Frank Micelotta/ImageDirect.

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.

Madonna wore a feminine, Versace dress

to Vanity Fair's Academy Awards afterparty in 2006.



Photo: Mark Mainz/Getty Images.

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."

Long before Kim Kardashian, Madonna took notes from Marilyn Monroe,

including for Madonna's 1991 Oscar's afterparty look.



Photo: Ron Galella/Ron Galella Collection via Getty Imag.

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.

In 1984, her "Like a Virgin" Video Music Awards

look blended punk and fairytale wedding perfectly.



Photo: Sonia Moskowitz/Getty Images.

Who thought wedding dresses could be punk? Madonna, that's who.

Daring looks celebrities wore on the BET Awards red carpet

Watch Next