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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ISLAND BEAUTY

Madonna's flirtation with the Spanish language and Latin culture began with the bilingual hit "La Isla Bonita." In the 1987 video, the newly brunette singer dances in a red ruffled flamenco dress to the sounds of guitar.