Madonna: 50 Looks We Can't Forget

As the Material Girl celebrates a half-century, trace her every fashion reinvention. By Aaron Parsley and Cara Lynn Shultz

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SURFER GIRL

A softer side of the singer emerged from the surf in the video for "Cherish," Madonna's surprisingly sweet 1989 love song. Directed by famed photographer Herb Ritts, Madonna – in a clingy black shirtdress – frolicked in the water and flirted with mermen.