Ivory arrived in Delaware in October of 1904 to begin his training with Pyle. Having already mastered the fundamental of figure drawing, he progressed quickly under Pyle’s instruction. By the autumn of 1905, Pyle was writing letters of introduction for the young artist to the editors of McClure’s Magazine and Collier’s Weekly, urging them to consider Ivory’s work. Like many of Pyle’s pupils, Ivory launched his professional career from the Pyle student studios at 1305 Franklin Street. In 1906, he received a major commission from the Saturday Evening Post to illustrate Joseph Conrad’s Mexican adventure tale, Gaspar Ruiz. Ivory had visited Mexico in 1904, and he was able to give his illustrations authenticity by relying on photos and costumes he had collected on his trip. Authenticity remained a key issue in his work, and he amassed a large collection of antique furniture, clothing, and guns to use as studio props.
Many other commissions followed Gaspar Ruiz, enabling Ivory to publish his work in most of the leading magazines of the period. Specializing in Western scenes, he caught the excitement and violence that characterized contemporary writers’ visions of the old West. His pictures also accompanied stories about the Far North, including several by Jack London. By 1909, Ivory had left the Pyle studios and, along with three other Pyle school alumni – W.H.D. Koerner, E. Roscoe Shrader, and Herbert Moore – set up a studio in the old Robinson house in Claymont, Delaware. There, the “four horsemen of Naamans”, as Shrader later called the group, pursued their professional careers. In 1915, Ivory and his wife spent the summer in California, Alaska, and the Yukon, where the artist took many photographs of the region as studies for later illustrations.
Although Ivory maintained a studio in Philadelphia for a short period in 1913 and 1914, he did most of his work in Wilmington until 1918, when he moved to New York City. There he joined a group of artists based in the Studio Building at West Tenth Street, and, in the company of artists like photographer G.W. Harting and writer-painter Kahlil Gibran, Ivory continued his efforts. By this time, however, the popularity of illustration was declining. Fewer and fewer commissions came Ivory’s way, and, with the onset of the Depression, his career was cut short. Although Ivory later painted for personal enjoyment after the traumatic effects of the Depression subsided, he no longer supported himself through his art.