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He Dressed Jackie Kennedy. 20 Years Later, He Was Selling Clothes at JCPenney: The Halston Story

By Old Money Allure 56:48 25,697 views on YouTube Mar 25, 2026

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This in-depth, full-length documentary explores how Roy Halston Frowick rose from Des Moines to design Jackie Kennedy's inaugural pillbox hat, conquered the 1973 Battle of Versailles, built a $150 million fashion empire... Show more

This in-depth, full-length documentary explores how Roy Halston Frowick rose from Des Moines to design Jackie Kennedy's inaugural pillbox hat, conquered the 1973 Battle of Versailles, built a $150 million fashion empire from Olympic Tower, then lost everything by signing away his trademark to Norton Simon, ending up locked out of his own showroom and dying unable to legally use his own name. ------------------- Gain FREE access to secret full-length documentaries on wealthy families "too scandalous for YouTube" by joining our newsletter: https://www.substack.com/@oldmoneyluxury ------------------- Roy Halston Frowick was born April 23, 1932, in Des Moines, Iowa, to accountant James Edward Frowick and Hallie Mae, learning to sew from his mother while growing up with an alcoholic father whose chaos drove the family to relocate to Evansville, Indiana. After leaving Indiana University after one semester, Halston moved to Chicago in 1952, working as a window dresser while taking night courses at the School of the Art Institute of Chicago. He began crafting women's hats inside Andre Basil's hair salon at the Ambassador Hotel before opening the Boulevard Salon on Chicago's Magnificent Mile in 1957, designing for celebrities including Kim Novak and Gloria Swanson. Diana Vreeland called him "probably the greatest hatmaker in the world" and "an absolute magician with his hands" after discovering his work in the late 1950s. At Bergdorf Goodman from 1958-1968, he managed the custom millinery department and became the store's first in-house designer to have his name placed inside the hats he created. On January 20, 1961, Jacqueline Kennedy wore Halston's signature beige pillbox hat to her husband's presidential inauguration, accidentally pressing a dent into the crown while holding it against Washington wind. The dented pillbox became the defining hat of the 1960s, with milliners across Seventh Avenue receiving orders for pillbox hats with intentional dents within days

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