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166. Hugh Hefner signature pajamas. Sophisticated bon vivant and founder of one of Playboy Enterprises, Hugh Hefner is truly a living legend. This signature wardrobe consists of black silk pajamas and burgundy crushed velvet smoking jacket trimmed with black cord and satin cuffs. The outfit was custom-made by Gary's Custom Tailoring – Beverly Hills, an exclusive tailor that only makes clothing for Hugh Hefner. Hefner donated his pajamas and world famous jacket for the unveiling of his figure to celebrate his 75th birthday in 2001. $1,000 - $1,500