Halston, now streaming, explores the life of legendary fashion designer Roy Halston Frowick, who rose to fame after designing the item in question.
The first time Jackie donned a pillbox hat was for John F. Kennedy’s 1961 inauguration, and, as it turns out, the look was somewhat accidental. According to Halston, Jackie actually dented his original design. “Funny thing about that pillbox hat,” Halston said during a 1966 interview, per Vogue. “It was made too small for her . . . but Mrs. Kennedy wore it anyway. When a gust of wind threatened to topple it from her head, she dented it hanging on to the hat. The Seventh Avenue copycat hat makers reproduced the design by the thousands so accurately that each pillbox had a dent in it.” How about that!
At the time, Halston was Bergdorf Goodman’s in-house milliner, and his career really took off after the inauguration, for obvious reasons. By the mid-1960s, he was designing clothes and befriending Hollywood’s elite, but not everyone seemed pleased with his success. Fashion designer Oleg Cassini — Jackie’s personal couturier who created a total of 300 looks for the former FLOTUS over the years — later insisted that accessorizing Jackie with a pillbox hat was his idea. According to Oleg, the pillbox was included in the sketches he provided Jackie ahead of the inauguration ceremony.