Julien's Auctions is running a large auction of Playboy founder Hugh Hefner's stuff, including several pairs of his pajamas, board games, a pipe, and this sharp smoking jacket. Described as "a scarlet silk damask smoking jacket with shawl collar and self-tie belt closure," the high estimate is $5,000 but I bet it goes for much more. According to Julien's, "All proceeds of the sale will benefit the Hugh M. Hefner foundation in support of organizations that advocate for and defend civil rights, with special emphasis on first amendment rights and rational sex and drug policies since 1964."
Hugh Hefner Bespoke Smoking Jacket (via Uncrate)