Adolfo began his career as a milliner and apprenticed at Balenciaga before moving to New York in 1948 to apprentice at Bergdorf Goodman. After receiving several awards for his hat designs, he opened his own millinery house in 1962 with a loan from Bill Blass. He began designing clothing for his models to wear while showing his hats and by the mid 1960s his celebrity clients ranged from the Duchess of Windsor, Gloria Vanderbilt, and Betsy Bloomingdale to Jackie Kennedy Onassis and Nancy Reagan who wore a red Adolfo dress, currently in the Smithsonian, to her husband’s second inaugural ball. In the 1960s Adolfo’s designs were playful and even flamboyant, though by the 1980s he was best known for his ladylike, Chanel-inspired cardigan suits.