Born second in a family of nine children in Maine and schooled in Boston, Willis attended Yale and traveled extensively in Europe. His sister was Fanny Fern, a member of the Pfaffian crowd. In 1831 he left Boston to join the editorial staff of the New York Mirror as a traveling correspondent discoursing on matters of taste and fashion. Like his fellow Pfaffians, Willis expressed admiration for the work of Edgar Allan Poe and even claimed an acquaintance with him.