Born at Martin's Ferry, Ohio, on 17 April 1908, to Ross and Mayme Buskirk Vandruff, Olive Freda Vandruff spent much of her childhood traveling in the Southwestern United States with her mining engineer father and her mother. Largely self-taught, Vandruff felt she received her artistic leanings from her father and grandfather. "Daddy and his father were artistically talented. They painted, but not professionally," she remembered in a 1963 interview for the "Amarillo Globe-Times".
Vandruff moved to San Antonio in the 1931 where she became an assistant to sculptor Pompeo Coppini and worked as a commercial artist. She considered Texas her home. About 1937 she married the engraver Charles F. Anderson, and with him ran an engraving business in San Antonio until the mid-1940s. Vandruff then studied with the painter Edmund Giesbert at the University of Chicago from 1946 to 1948.