Estelle Massey Osborne was born May 3, 1901, the eighth child of William H. and Betty Estelle Massey. A native of Palestine, Texas she attended local public schools before beginning teacher's training at Prairie View State Normal and Industrial College. After two years Osborne received a certificate and began her career as a public school teacher. Her teaching career ended when an act of violence committed at the school almost resulted in her death.

It was at this time that Estelle, encouraged by her brother Edward, a dentist in St. Louis, Missouri, decided to pursue a nursing career. She began her training at City Hospital No. 2 in St. Louis. She later received the first scholarship awarded to a black nurse by the Julius Rosenwald Fund and continued her studies at Columbia University, where she received a Bachelor of Science degree in 1930 and a Master of Arts degree in 1931.

Estelle Osborne opened many doors for black nurses. She was the first black superintendent of nurses and director of the nursing school at Homer G. Phillips Hospital in St. Louis (1940-1942) and the first black nurse to receive a Master of Arts degree with a major in nursing from Teacher's College, Columbia University. In 1949 as a member of the board of directors of the American Nurses Association, she was an official delegate to the International Council of Nurses in Sweden. Upon her appointment as a consultant in 1943 to the Coordinating Committee on Negro Nursing for the National Council for War Service, she became the first black person to hold an office on the staff of a national nursing organization. Osborne's other career achievements include becoming head nurse at St. Louis City Hospital No. 2.

Osborne also taught at the Central Nursing School of Lincoln Junior College in Kansas City, Missouri (1972) as well as at the Harlem and Lincoln Schools for Nurses in New York City (1929-1931). She was later appointed Educational Director at Freedmen's Hospital in Washington, D.C. In 1934 Mrs. Osborne went to work as a researcher to undertake studies of rural life for the Rosenwald Fund. Through her efforts, black colleges in the South were able to benefit from federal provisions established to aid nursing education. From 1934 to 1939, Mrs. Osborne served as the eleventh president of the National Association of Colored Graduate Nurses, and in 1947 she was selected to join the faculty of the Department of Nursing Education at New York University. Osborne was also Assistant Director of the National League for Nursing (1959) and Associate Professor of Nursing Education at the University of Maryland (1954); chairman of the Local Program Committee, National Council of Negro Women; a member of the U.S. Cadet Nurse Corp; an Advisory Committee member of Harlem Hospital School of Nursing; a member of Key Women of Greater N.Y., the National Association for the Advancement of Colored People and the National Urban League.

In 1946 Estelle Massey Osborne was the recipient of the Mary Mahoney Award for her contributions to the field of nursing. She was cited for her efforts to open professional opportunities to minority groups. In 1959 the New York University Department of Nursing honored her as “Nurse of the Year”, and the Estelle Massey Scholarship was established in her honor at Fisk University.

Estelle Massey was married to Dr. Bedford N. Riddle in 1932. In 1947 she married Herman Osborne.