An elaborately carved oak chair with a leather upholstered seat and nail head trim.

A group of 132 brown leather-bound volumes of Playboy magazines from Hugh M. Hefner's personal collection kept in his office at the Playboy Mansion. The collection begins with Volume 3, dated 1956, and ends with Volume 60b, which contains issues through 2013.

A burgundy smoking jacket with black silk pajamas and slippers, personally owned by Hugh Hefner. To elevate his signature silk smoking jacket and silk pajama look for public outings, Hefner often opted for a sleek velvet smoking jacket such as this to wear over his silk pajamas. Hefner was pictured wearing velvet evening jackets in this style on various occasions as well as home at the Playboy Mansion.

This painting hung in the Study of the Playboy Mansion West.

The acetate teddy-style bomber jacket in a plush pink with black accents, with the back featuring a custom embroidered company logo with black, white, and red thread with "Twenty-Fifth Anniversary" embroidered cursive lettering done in black thread.