[3] He then attended the Santa Fe Indian School, where he studied art under Dorothy Dunn from 1935 to 1937.

[4] After working under Dunn, Nailor spent a year studying with Kenneth M. Chapman and the Swedish muralist Olle Nordmark.

Nailor met his future wife, Santana Simbola, who was working as a nurse at the Santa Fe Indian Hospital.

In 1937, with his good friend the artist Allan Houser (Chiricahua Apache), he set up a studio in Santa Fe to paint and work on his silkscreen prints.

[1] In 1939, Nailor, Houser and Velino Shije Herrera were commissioned by the Section of Painting and Sculpture to paint murals in the Main Interior Building in Washington, D.C.[5][6] In 1942, Nailor was selected for the commission for a mural for the Navajo Nation Council Chamber in Window Rock, Arizona, to depict the history of the Navajo people.