Born in Sacramento, Otis Oldfield attended Marshall Primary and Sutter High School, but quit school at 16 to work at Chaney’s print shop. He moved to San Francisco in 1908 and began his official art training with Arthur and Alice Best at Best’s Art School, working nights to save money for study in Paris.

In Paris, Oldfield enrolled at the Académie Julian in 1911 and studied there for two years. During World War I, he moved to Bouffemont and apprenticed as a book binder. He returned to Paris in 1918 and opened a studio in Montmartre.

Oldfield returned to Sacramento in 1924 but stayed only briefly before moving to San Francisco and becoming an instructor at the California School of Fine Arts. In 1926, he married one of his students, Helen Clark, a talented painter of landscapes, figures, and still lifes, who had previously studied at the California College of Arts and Crafts in Oakland. It was at the couple’s Telegraph Hill home and studio that Oldfield painted his self portrait and this portrait of Helen. This and other Oldfield paintings depicting Helen were criticized because he often portrayed her nude or in undergarments. In order to diffuse any possible controversy related to this painting when he sent it to an exhibition in Los Angeles, he entitled the painting White Dress, instead of using his original title, White Nightie.

Oldfield began to receive wide recognition, and in 1933, his work was included in an exhibition of American art at the Whitney Museum in New York. The following year the federal government hired him to paint murals in San Francisco’s Coit Tower. He was then accorded a solo exhibition at the San Francisco Museum of Art and went on to medal at the 1939 Golden Gate International Exposition.

In 1946, Oldfield became assistant professor of painting and drawing at the California College of Arts and Crafts in Oakland. That year, he purchased a summer home in Gold Run, but later moved to nearby Alta, producing scenes of the Sierra and the Gold Country’s historic sites. He left his teaching position in 1952, but continued to teach evening classes in his home. He made art until his death in San Francisco in 1969. Helen Clark Oldfield continued to paint and exhibit for 12 more years.