Douglass probably received her earliest artistic training from her mother, who taught art at the Alabama Conference Female College (later renamed Huntingdon College). In 1899, Douglass moved to Birmingham and within two years was listed in the city directory as an art teacher and artist. She began her career as china painter and watercolorist.
In 1908, she began her studies at the Art Students League in New York City, where pupils studied the human figure by drawing and painting from live models instead of plaster casts of classical sculptures. The Birmingham Museum of Art has a large collection of Douglass' life drawings from this period. Douglass later took up printmaking, the medium for which she is best known. Her detailed scenic etchings of China and Cambodia can be found in the collections of the Library of Congress and the Metropolitan Museum of Art. She died in 1935.