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Michael Jackson 1958-2009

Michael Jackson's 10 Most Iconic Looks

From one glove to white socks to military jackets, see how Jackson set trends for a generation and hear the scoop on the behind-the-scenes team responsible for the styles.

FITS LIKE A GLOVE

Setting off a massive trend, Jackson wore just one bedazzled glove to the 1984 Grammys along with a sequined military jacket, complete with gilded sash. Not only did he get fashionistas buzzing, he also picked up a record-breaking eight awards that night. Jackson was very into “British regalia show clothes – over the top military themed items,” says longtime costumer Michael Bush, who would research historically correct military gear for Jackson, and then “do a street version, rock and roll look out of plastic, vinyl. Anything other than what was traditional!”