Jackson was known for his distinct and ornate wardrobe on stage and in his videos. “Something he wore in an iconic performance that there’s only one of [would be valuable],” says Reeder. In April 2007, Heritage sold a long, black “backwards” tuxedo jacket Jackson wore on stage in 1993 for $956 at auction. Today, that jacket could fetch as much as $2,500, Fleisher says.

Photos: Getty Images, Christie's, eBay.
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