Look Back at Madonna's Best Outfits Ever

1984

At the first annual MTV Video Music Awards, the icon was the perfect "edgy virgin bride" in a lingerie wedding dress, cheeky "boy toy" belt, and fingerless gloves. She admitted to doing her own makeup, topping off her look with a red lip. "Red is the sexiest a mouth can ever look," says makeup artist Pat McGrath. "It's dangerous too. Very Madonna, and very Hollywood."

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1985

It was Madonna's world and we were all living in it! In her "Material Girl" video, the star was the picture of luxury in an over-the-top hot pink dress (one of the first of many looks she has worn à la Marilyn Monroe). Covered in plenty of diamonds and surrounded by fellas, she was a star and fashion icon on the rise.

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1987

To pick up her Favorite Pop/Rock Female Video Artist trophy at the American Music Awards, the star channeled Monroe again in a body-hugging dress and majorly bold brows. "The red lips and beauty mark were her signature at the time," says makeup artist Gina Brooke.

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1988

Continuing her streak of bold beauty looks, Madonna showed off in an LBD with cutouts and an oversized denim jacket. "She's great at picking up the next big thing," says DSquared2 designer Dan Caten.

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1989

Her outfits of lacy under-outerwear accessorized with dime-store bangles and crucifixes made her a fashion icon to thousands of wannabes. Here, the singer gave an electric performance on stage in a pair of baggy trousers that she sexed up with a lacy corset top.

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1990

Hello cone bra! Madonna debuted her iconic Jean Paul Gaultier top while performing during her Blonde Ambition tour. "She doesn't take on trends, she creates them," says hairstylist Andy LeCompte. "That's why she likes taking risks."

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1990

Only Madonna could commands courtiers to "vogue" at the MTV Video Music Awards! She gave an epic performance of her hit song of the same name in a Material-Girl-meets-Marie-Antoinette ensemble.

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1995

Talk about a style 180! At the MTV Video Music Awards, the star proved her ability to make menswear sexy by exposing her bra and adding a major updo. "This is very Catherine Deneuve in Belle de Jour—big hair with lots of teasing," says hairstylist Garren.

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1996

"Only I could understand her passion and pain," Madonna said of her role in Evita. For the premiere of the film, she wore a sophisticated red satin Christian Dior number and head topper that channeled the late Eva Perón, but still felt sexy. "It's a brilliant look for Madonna, fantastic," says hairstylist Martin Samuel.

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2003

In the MTV Video Music Awards opening number (which contained two of the most talked about kisses in history), Madonna's menswear look contrasted that of virgin "brides" Britney Spears and Christina Aguilera. Post-show a ruckus ensued, proving that the singer could still create headlines. "She's always up for the unexpected," said the VMA's executive producer Salli Frattini.

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2005

This wasn't the first time the icon went without pants, and it wouldn't be the last. At the MTV European Music Awards, Madonna was "Hung Up" in a purple bodysuit, matching leather jacket, and knee-high boots.

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2006

Where Madonna goes, a fabulous party always seems to follow. The star revealed her feminine side at the Vanity Fair Oscar Party in a plunging ruched Versace dress that gave "pretty in pink" a new meaning.

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2009

At the Metropolitan Museum of Art's Costume Institute Gala, the singer chose a bold Louis Vuitton creation and out-of-this-world headpiece that certainly got people talking. "I don't trust anyone else's taste but my own," Madonna said.

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2011

Madonna looked ravishing at the Venice Film Festival in a custom-made Vionnet gown adorned with red butterflies and a pair of glittering sunglasses. "Madonna is a chameleon," says stylist Arianne Phillips, "so she makes the most beautiful canvas."

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2012

Look up "fabulous" in the dictionary, and you'll see Madonna's name. At the premiere of W.E., the star nailed the red carpet in an organza and velvet Marchesa design that oozed elegance — a far cry from many of her more flamboyant outfits.

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2012

For an epic appearance at the Super Bowl XLVI Halftime Show, the singer proved she can go from elegant to outrageous in one minute flat. The star performed in a custom Givenchy costume that crossed a Roman gladiator with Cleopatra. "I think you have to try on a lot of guises before you know who you are," Madonna said.

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2012

Bra-bra-bra-voom! Never one to keep perfectly good lingerie hidden, she brought back her classic cone bra silhouette during her her MDNA Tour in London.

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2013

No pants, no problem! At the Costume Institute Gala for the Punk: Chaos to Couture exhibition, Madonna took on the theme in head-to-toe Givenchy Haute Couture complete with a black wig making sure to grab attention.

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2013

Madonna: model boy scout? At the 24th Annual GLAAD Media Awards, the queen of controversy showed her support by making a political statement and adding a rebellious edge to her spin on the traditional uniform.

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2014

What a glove! Madonna made headlines in a Ralph Lauren tuxedo and matching black hat that was chosen by her son, David (who wore a similar look), at the 56th Annual Grammy Awards. "She never does anything halfway," says designer Catherine Malandrino. "When she was breaking sexual taboos, she did it totally. When she decided to become a mom, she did it totally."

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2015

Madonna arrives at the 57th annual Grammy Awards in Los Angeles — REUTERS/Mario Anzuoni

Madonna is in charge! Following the release of her music video "Living for Love," the first off her 13th studio album Rebel Heart, the singer carried over the video's matador theme onto the Grammys red carpet in a custom black and lilac Givenchy ensemble that had everyone doing a double take.

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2016

At 57 years old, the singer proved she can still turn heads. She showed up for the 2016 Met Gala in a breast-bearing cutout ensemble that put on a cheeky display from behind.

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2016

The style icon gave a moving tribute performance to another of fashion's greatest stars at the 2016 Billboard Music Awards. Madonna honored her late friend Prince in a paisley purple three-piece suit with Victorian ruffle detailing on the sleeves. She completed her look with wild curls, platform shoes, and a bedazzled baton.

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2017

Madonna and Moschino: a match made in fashion heaven. The superstar wore a camo design by Jeremy Scott for Moschino at the 2017 Met Gala; it may not have quite fit the "Rei Kawakubo/Comme des Garcons: Art Of The In-Between" theme, but hey, she's Madonna.

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2018

On the other hand, for the "Heavenly Bodies: Fashion & The Catholic Imagination" Met Gala in 2018, Madonna was right on theme in her Jean Paul Gaultier gown. Fittingly, she also performed at the event.