Fashion Evolution: Madonna

Twenty-five years after her self-titled album introduced an entire generation of women to lace fingerless gloves, Madonna is back with her 11th studio creation, Hard Candy. And while we love to "Get into the Groove" as much as the next gal, we're even more obsessed with Madonna's quarter century-long reign as a fashion icon. The queen of reinvention has been a trendsetter since day one -- but that doesn't mean she's always gotten it right!

Frank Micoletta - WireImage

Desperately Seeking Susan 1985
With her sophomore album Like A Virgin, Madonna hit the mainstream. Constant rotation of her videos on MTV combined with her first major film role inspired women around the world to copy her bad-girl look.

Everett Collection

Pounding the Pavement 1990
At age 32, Madonna was already obsessed with keeping her phenomenal bod in shape. This multicolored mess was the pinnacle of early '90s workout chic!

Ron Galella, WireImage.com

The Blond Ambition Tour 1990
Jean Paul Gaultier designed the iconic cone bra costumes for Madonna's smash tour and suddenly, lingerie as outerwear was everywhere!

Frank Micoletta

Truth or Dare Premiere 1990
Only Madge could walk a red carpet in little more than a jeweled body suit, thigh-high stockings and a shock of black hair. We don't even know what to say about her beloved backup singers' jumpsuit.

Kevin Mazur, WireImage.com

Madonna and Michael Jackson 63rd Annual Academy Awards 1991
Who needs Halloween when you're Madonna? The Oscars were just as good a reason to dress up like Marilyn Monroe with one key accessory -- Michael Jackson!

Ron Galella, WireImage.com

"Sex" Book Party 1992
Madonna couldn't decide if she wanted to look like the naughty version of Little Bo Peep or the naughty version of Heidi at the launch party for her controversial photo book "Sex" -- so she chose both!

Kevin Mazur, WireImage.com

With Honors Premiere 1994
Madonna's sari-inspired ensemble showcased her famously toned abs and marked the beginning of her fascination with global fashion.

Barry King, WireImage.com

The American Music Awards 1995
Posing with super producer Babyface, Madonna added red lips and her trademark blond locks to a traditional Chinese dress.

Jim Smeal, WireImage.com

"Bedtime Stories" Party 1995
To celebrate the release of the 6th studio album Bedtime Stories, Madonna hosted a sleepover themed fiesta that was broadcast on MTV. Ironically, at the one event where lingerie was the dress code, the singer looked relatively covered up in a leopard print jacket and white silk dress.

Ron Galella, WireImage.com