His art had several influences: study in the Summer Art School in Glacier National Park (Montana) with New York portrait painters Winold Reiss and Carl Linck; the cowboy school of painting led by Charles Russell; the Oklahoma school of Indian painting; the Banff Centre School of Fine Arts (now the Banff Centre for Continuing Education); and the Provincial School of Technology and Art in Calgary.
In the main, his work exhibits a romantic and nostalgic vision of his Blood people's life in the late 19th century. Thus, it features warriors in their traditional activities of warfare, hunting and ceremonial life. Tailfeathers later began experimenting with cast-bronze sculpture that depicted themes inspired by cowboy art, which he had studied on a 1969 visit to the Arizona studio of George Phippin.