People.com Celebrity 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. By Melissa Liebling-goldberg Updated on June 24, 2021 11:38 PM Share Tweet Pin Email 01 of 10 MUST-HAVE JACKET Time & Life Pictures/Getty For his 1982 teen gang video "Beat It," the singer picked a casually cool outfit that would inspire millions to wear zipper-accented red leather jackets in a decade-defining look for the '80s. 02 of 10 SUITED UP Eugene Adebari/Rex USA From the moment Jackson danced across the lighted floor in the 1983 video for "Billie Jean," legions of teenagers wanted his slick leather suit, pink shirt and red bow tie. 03 of 10 MOONWALK MOMENT Globe Debuting the moonwalk live at the Motown 25th Anniversary celebration in 1983, the dancing star wore his signature cropped pants - designed to show off his intricate footwork to its fullest - with sparkling socks, shirt and his omnipresent penny loafers. Ken Luftig Viste, curator of the Grammy Museum's Michael Jackson: HIStyle exhibition, explains, "He'd wear an elaborate outfit like this so that even the people in the farthest rows could see him dance because the crystals are flashing under the lights.The white socks really also showed off the way he danced, the ways he could move and how much of that was footwork," says Luftig-Viste. "He wanted people to be able to see him dance." 04 of 10 FITS LIKE A GLOVE Ron Galella/WireImage 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!" 05 of 10 'BAD' MOVE Shooting Star The singer went for a distinctly edgier style for his Bad album in 1987, adding heavy eyeliner to a buckled leather jacket and skintight jeans. 06 of 10 DANGEROUSLY STYLISH 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! 07 of 10 STRAPPED IN Frazza/AFP/Getty Never one to shy away from theatrical embellishments for his stage costumes, the singer hit the road in 1988 in second-skin outfits covered in SampM-inspired straps. 08 of 10 STAGE SHOW Frank Micelotta/Getty Flanked by similarly dressed backup dancers, Jackson took to the stage of the 1995 MTV Video Music Awards in a black suit, skinny black tie and - ever provocative - white arm band. 09 of 10 WHITE OUT Ramey Talk about a united front! The singer enters for a court date, with his sisters LaToya and Janet, in white head-to-toe in 2004. 10 of 10 GOLDEN AGE Fame In the past several months, Jackson began stepping out in fashionista-favorite womenswear labels, including Balmain and this Givenchy by Riccardo Tisci studded T-shirt and blazer.