The beginnings of The Dress Barn can be traced to 1962, when Elliot Jaffe was working as a merchandising manager for Macy's Department Store in Connecticut. He approached his wife, Roslyn, with an idea for a women's discounted apparel store, and the two decided to begin planning a test store. Knowing that they needed a reliable source of income to support their children, Jaffe retained his job at Macy's as he and Roslyn worked after-hours to open the first Dress Barn store later that year in Stamford, Connecticut.