Madonna’s 10 Greatest Fashion Hits

As Madonna’s greatest hits album, Celebration, hits stores, we look back at the queen of reinvention’s best moments

-Kathryn H. Cusimano

Singers come and singers go, but Madonna remains. How has she remained a star for more than two decades when other, better, singers, have fallen by the way side. Simple. She’s the queen of reinvention: she changes her image before anyone has a chance to get bored with her. In honor of the release of her new greatest hits album, Celebration, we look back at the Material Mom’s best fashion moments.

Pushing Borderlines
Madonna’s lyrics and melodies may have been sugary-sweet pop, but her style was most certainly rebellious. On the heels of the slick disco era, she burst on the scene in 1984 with wild, two-tone hair, leather, denim, see-through shirts and piles of necklaces and rubber bracelets.

Madonna/Whore Complex
The ultimate good girl gone bad ditched the black bra, mesh shirt and bracelets for white lace and a Boy Toy belt for her VMAs performance of “Like a Virgin.” Sure, she looked like a bride, when then she lifted her veil and proceeded to writhe across the stage while singing about being touched for the very first time — inspiring a generation of underage girls to do the same (ahem, Britney).

Like a Prayer
Madonna toyed with religious icons in her 1989 video for “Like a Prayer.” With her dark curly hair and crucifix necklace, she could almost be mistaken for a good Italian Catholic girl – but the burning cross gives her away.