Halston's Connection To The Kennedy Family Explained

Before becoming an American icon and world-renowned designer, Roy Halston was a notable milliner. At a young age, Halston was taught to sew by his mother which led to him making hats for his sister (via British Vogue). After studying at Indiana University and then the School of the Art Institute Chicago (via Biography), he discovered his love of designing hats that were displayed at the Chicago Ambassador Hotel by hairdresser André Basil.

Halston found a lot of success in the Windy City, even opening his own salon on North Michigan Avenue (via the Chicago Tribune). But he soon made the move to the Big Apple to work as a designer for milliner Lily Daché in 1959. Halston took up residence at Bergdorf Goodman, a luxury department store on Fifth Avenue (via Culture Trip). Here he became the store's first in-house designer, and would eventually establish his own millinery company in 1968.

By the 1960s, Halston had become Jackie Kennedy's hat maker (via Refinery29). He's the creative mind behind that pillbox hat moment at John F. Kennedy's 1961 inauguration (via Live About).

Described as a "defining moment" for Jackie's fashion legacy by Esquire, the hat was actually a little too small for her. "But Mrs. Kennedy wore it anyway," Halston said in a 1966 interview with Vogue. "When a gust of wind threatened to topple it from her head, she dented it from hanging on to the hat," he explained, adding that the copycat hat makers on Seventh Avenue replicated this design "so accurately that each pillbox had a dent in it." Halston would later go on to say that he found this hilarious. "So during all the ceremonies it had a dent in the hat, so everybody who copied it but a dent in it, which is so funny," he told a reporter at the time (via InStyle).

The hat also garnered a little controversy, too. As PopSugar notes, when The New York Times said that Halston was the designer of the pillbox in a 1973 profile, fashion designer Oleg Cassini –- who was also Jackie's personal courtier –- insisted that the pillbox was his idea, and that he had sketched the initial design. This revelation was featured in the 1991 book "Simply Halston: The Untold Story" by Steven Gaines. "A pillbox hat may not be important, but the truth is," Oleg is quoted as saying in the book.

Whatever the truth may be, it's undeniable that this hat catapulted Halston into the mainstream, and cemented him as one of America's most recognized designers.