03/05/2026 General, Books & Autographs
“Miss Head has designed a number of staggeringly sumptuous outfits and some that are done for fun, yards of fur, acres of chiffon. They tread that delicate line between burlesque and reality; the women in the audience know they aren't anything anybody could wear, but oh! how lovely if one could!”
-- James Powers, The Hollywood Reporter, 1964
The 1964 film What a Way to Go! is a stylish comedy directed by J. Lee Thompson and starring Shirley MacLaine at a peak moment in her career. The screenplay by Betty Comden and Adolph Green follows MacLaine’s character, Louisa May Foster, a four-time widow whose husbands are played by an extraordinary roster of leading men—Dick Van Dyke, Paul Newman, Robert Mitchum, Gene Kelly and Dean Martin—the first four leaving Louisa increasingly surrounded by extravagant luxury.
Central to the film’s visual appeal were the costumes by the legendary designer Edith Head. Given a remarkable costume budget of more than $500,000—one of the largest of her career—Head created an extraordinary wardrobe for MacLaine that charted Louisa’s transformation from a naïve small-town girl into one of the richest women in the world. The screenplay called for over 70 costume changes, becoming more flamboyant and reinforcing the film’s satire of wealth, glamour and Hollywood excess.
The film’s fashion spectacle was amplified by a collaboration with the jeweler Harry Winston, who loaned approximately $3.5 million worth of diamonds for MacLaine to wear on screen. The most famous example is the celebrated “Diamond Dress” worn with a suite of genuine Winston jewels—including a necklace, earrings, bracelets and diamond hair ornaments valued at roughly $2.5 million.
The film became one of the most elaborate costume showcases of the 1960s and earned Edith Head an Academy Award nomination for Best Costume Design. Today, What a Way to Go! is remembered as a campy yet dazzling Hollywood spectacle—a lavish fusion of Shirley MacLaine’s star power and Edith Head’s extraordinary imagination in costume design.
(Above L-R): Black mourning dress with veil worn in the film’s opening scene and at the Internal Revenue Service. / Beige ensemble trimmed with mink worn in Robert Mitchum's plane.
The following designs appear in the 5-minute film-within-a-film "Lush Budgett"—a fantasy dream montage that satirizes the excesses of 1960s Hollywood glamour.
(Above) Two sketches of the iconic “Diamond Dress” encrusted with rhinestones and crystals and weighing an estimated 10-15 pounds. MacLaine was festooned with diamond jewelry from Harry Winston in one of the most lavish uses of jewelry in Hollywood history. Crew members reportedly gasped the first time MacLaine appeared on set wearing all the pieces.
(Above L-R) The infamous “Backless Dress” worn seated at a table, featuring a long pearl necklace draped seductively down her exposed back. / White dress with fur-trimmed wrap and fur muff worn when she emerges from a Lincoln Continental.
(Above L-R) Emerald satin dress with cascading ribbons which she dramatically unfurls as she enters a party. / Asian-inspired, form-fitting red vinyl dress with bubble peplum accessorized with a red fan.
(Above L-R) Flirty babydoll of pale blue satin trimmed with marabou feathers worn in a bedroom scene with Robert Mitchum. / Dress with fur-trimmed cape, possibly a version of the yellow ensemble worn when she emerges from a Lincoln Continental.
Auction Wednesday, March 18 at 10am
Exhibition March 14 – 16
Lot 141
Ten original Edith Head costume sketches for Shirley MacLaine in What a Way to Go!
View Lot