Designer Oleg Cassini is best known for his work with First Lady Jaqueline Kennedy, helping her create her signature look. Before that time, however, Cassini had a successful career in Hollywood. He began as a designer in Rome in the 1930s. Then, he moved to America and became a costume designer at Paramount alongside Edith Head. In 1941 he married Hollywood star Gene Tierney, and he would design the gowns for all of her films until their divorce in 1953.

This red velvet dress, designed by Cassini, was first worn by Gene Tierney as Morgan Taylor in the 1950 film Where the Sidewalk Ends. Chesterfield Cigarettes frequently used Hollywood stars to advertise their products, and not long after Where the Sidewalk Ends, promotional photos from the film were used to create an ad featuring Tierney in the dress. However, when she was offered the dress to keep, she declined, stating it was far too challenging to walk in. 

The dress went to Cassini’s private salon on 16 East 55th Street, where Marilyn Monroe purchased it. In 1950, Marilyn wore the gown in a series of promotional photos by Eric Carpenter for her film The Asphalt Jungle. In 1952 she wore the dress again at the Henrietta Awards (Later renamed the Golden Globes), where she received an award for “Best Young Box Office Personality.” She appeared in a promotional photo from the evening alongside fellow nominees Tony Curtis, John Derek, Leslie Caron, Virginia Gibson, and Mitzi Gaynor.

The book Marilyn in Fashion: The Enduring Influence of Marilyn Monroe states that:

Commenting on the design, Marilyn commented to Modern Screen, “I’ve always admired [Cassini’s] taste and imagination of women’s clothes, and my gown is no exception. It fits snugly down to my knees and then flares out, in the Lillian Russel tradition.” With a straight face she added, “It plunges somewhat in the front, but not extremely.” One fan magazine declared the gown the most risqué design of the year.