Hugh Hefner’s Legendary Smoking Jacket and a Marilyn Monroe Dress and Are Heading to Auction

A pair of 20th century American icons will share the billing yet again this spring.

In March, belongings once owned by the late Playboy founder Hugh Hefner and actress Marilyn Monroe will land at Julien’s Auctions. The three-day sale named “Property from the Playboy Archives and The Hugh M. Hefner Foundation, and Property from the Life and Career of Marilyn Monroe” will take place in Los Angeles from March 28 through March 30. Over 1,000 artifacts from the duo will be up for grabs with ties to Hefner’s early life and Playboy’s peak era, plus film wardrobe and photography once belonging to Monroe.

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Hefner's classic smoking jacket and pajamas and a Andy Warhol silkscreen in the Julien's Auctions sale.
Hefner’s classic smoking jacket and pajamas and an Andy Warhol silkscreen in the sale.

The Playboy Enterprises collection being offered at Julien’s will feature a number of highlights dating back to 1950s. A LeRoy Neiman oil on canvas painting from 1956 carries the highest sales estimates from Hefner’s possessions at $60,000 to $80,000. The runner up lot is an Alberto Vargas original watercolor drawing of a Vargas Girl pinup, from the 1967 issue of Playboy. Experts estimate it could fetch between $30,000 and $40,000 at auction. Other highlights from the ladies man include his classic red smoking jacket with silk pajamas, slippers, and a smoking pipe (estimate $2,000-$3,000) and an original Andy Warhol “Playboy Bunny” silkscreen.

The costume worn by Marilyn Monroe as Lillian Russell for a pictorial feature in Life magazine’s December 1958 issue is one of the most eye-catching lots from her collection. The lavender satin, boned leotard with draped chiffon sashes is estimated to sell for between $20,000 and $40,000. A Mae West-inspired black and cellophane effect evening gown designed by legendary costume designer William Travilla—worn by Monroe in 1955’s The Seven Year Itch—boasts the highest sales estimate, however, for between $100,000 and $200,000.

Marilyn Monroe's floret diamond brooch (left) and Life magazine costume (right) offered in the Julien's Auctions sale.
Marilyn Monroe’s floret diamond brooch (left) and Life magazine costume (right) offered in the sale.

Other lot highlights from Monroe include her 1962 John F. Kennedy birthday gala original program and ticket stub (est. $4,000-$6,000), her custom shade of Elizabeth Arden lipstick in a gold tone case (est. $7,000-$9,000), and a floret diamond brooch (est. $8,000-$10,000).

Both born in 1926, Monroe and Hefner’s legacies are forever linked. The magazine founder’s inaugural 1953 issue of Playboy featured the Some Like It Hot actress as a centerfold. Its release launched the success of the men’s publication and made Monroe an instant household name and sex symbol. The two were never a couple but they are now laid to rest side by side at Westwood Village Memorial Park in Los Angeles, following his death in 2017.

Julien’s Hefner and Monroe auction will kick off Thursday, March 28 at 10 am live in L.A. and online, with sale ending on Saturday, March 30.

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