Madonna's Most Iconic Looks Ever

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 now infamous 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."

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 men, she was a star and fashion icon on the rise.

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.

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

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.

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."

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.

In full-on Marilyn Monroe mode at the 63rd Annual Academy Awards, Madonna celebrated with Michael Jackson in a white hot, old Hollywood glam look that included a luxe fur cape and $20 million worth of Harry Winston diamonds.

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.

"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.

R-E-S-P-E-C-T! The then new mom was radiant in Dolce amp Gabbana (but didn't lose her signature accessory—gloves) at the 54th Annual Golden Globe Awards, where she took home the Best Actress award for Evita. "The film gave me time off from being me," she said.

Enamored with Arthur Golden's 1997 book, Memoirs of a Geisha, Madonna channeled her latest influence by performing "Nothing Really Matters" in a kimono at the Grammy Awards.

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.

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 showed off her fit figure in a demure purple bodysuit, matching leather jacket, and knee-high boots.

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.

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 many called more than unique. "I don't trust anyone else's taste but my own," Madonna said.

From crazy to beautiful! 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."

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.

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.

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 and proved that she was the sexiest mom alive.

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.

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.

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."

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. 

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. 

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 3-piece suit with Victorian ruffle detailing on the sleeves. She completed her look with wild curls, platform shoes, and a bedazzled baton.