He then opened his own hat business in 1953. His hat business was very popular. Halston’s hat designs brought the fantastic to whimsy; he used all manner of jewels, flowers and fringe to decorate hoods, bonnets and coifs. A lot of famous people bought his hats. For example, radio actress and comedian Fran Allison was the first person to buy a hat. Also, Kim Novak, Gloria Swanson, Deborah Kerr, and Hedda Hopper all bought hats from his store.
Halston’s “big break” was when Chicago Daily News did a story about his fashionable hats. The news article helped his popularity a lot. It helped him open his own shop called the Boulevard Salon. After this store, Halston moved to New York City to work for milliner Lilly Dache. A year into working with her, he was named co-designer at Dache. This helped him become acquainted with several fashion editors and publishers. He left Dache to become head milliner for department store Bergdorf