In 2000, Azzuolo relocated to New York where he began freelancing in the fashion industry. In 2006, he joined Ralph Lauren as design director for Ralph Lauren Purple Label and Ralph Lauren Black label before launching his custom hand-tailored collection, a.a. antonio azzuolo, in 2008.
Azzuolo lends focus to New York street style, which he translates through a refined lens. He incorporates the craft and luxury he learned in Europe with an unexpected whimsy and certain naivete. With every collection he explores youth archetype while expanding on his concept of building the fundamentals of a man's wardrobe.