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.


Jackson hearkened back to an earlier era for his '20s-inspired video for "Smooth Criminal" in 1987. Forget the tommy guns – fans were blown away by his sharp tailoring and matching fedora!