An itinerant artist, Ammi Phillips traveled throughout Massachusetts, Connecticut, and New York to find subjects who wanted their portraits painted. While not professionally trained, he was very prolific and produced hundreds if not thousands of works. His style changed over the course of his career, reflecting the fashion of the times to keep up with current tastes. In Woman in Black Ruffled Dress, he paid particular attention to the ruffled collar of his subject and her evenly curled hair.