27 of Madonna’s Most Iconic Red Carpet Moments

Madonna captured everyone’s attention when she attended the first MTV Video Music Awards in a lacy white number paired with a boundary-pushing “Boy Toy” belt.

The singer wore another layered necklace look when she posed for a photo at the American Music Awards in a black bustier styled with fingerless gloves.

Madonna arrived at the opening of her film Desperately Seeking Susan in an all-white ensemble featuring a white fur stole, plenty of pearls, and a deep red lip.

The singer stunned on the 1987 American Music Awards red carpet when she posed in an iridescent off-the-shoulder gown and dark makeup.

The “Express Yourself” songstress opted for a dark gray two-piece set for the 1991 Cannes Film Festival.

She wore a custom Bob Mackie gown to the 1991 Academy Awards. The getup was nothing short of glamorous. Between the extravagant diamond jewelry and the meticulously styled hair, how could you not love this look?

How fun is this bedazzled bodysuit she wore to the Truth or Dare film premiere?

Madonna looked oh-so-cool while rocking a pair of dark shades at the premiere of A League of Their Own.

For the Bedtime Story premiere in 1995, she strolled down the red carpet in a slinky white slip dress and a printed leopard ankle-length coat. Her pinned curls and red lips sealed the deal.

The award-winning singer chose a more casual look for the 1995 MTV Video Music Awards. She wore a silky teal top tucked into belted black pants. Her pulled-back hair complemented her outfit perfectly that night.

The singer shined at the 1997 Golden Globe Award in a black bustier gown with matching opera gloves. She won the award for Best Actress that night for her role in Evita.

She sported a gorgeous floral cape while walking into a Tony Awards party in 1998.

The superstar attended the 2000 MTV European Music Awards in a sequined red two-piece set.

Madonna bundled up in a tweed-trimmed coat while walking the Cannes Film Festival red carpet in the early 2000s.

In 2005, she donned a stunning purple ensemble featuring black fishnets and knee-high croc-embossed boots.

For the I Am Because We Are premiere in Cannes, the singer wore a drapey sequined gown by Chanel.

Madonna chose a rose-pink long-sleeved silky number to attend amfAR’s Cinema Against AIDS event.

Madonna wowed fans at the Met Gala red carpet when she arrived in an intricately designed blue ensemble that featured a sculptural headpiece.

Two years later, she attended the Met Gala again, this time in a satin Stella McCartney gown, vintage Cartier jewels, and a Christian Dior clutch.

The singer wore a gorgeous green Reem Acra gown to the 2012 Golden Globes. The metallic bodice and basket-weave skirt are something else.