[1] Mildred Inez Caroon was born in Fort Barnwell, North Carolina, and raised in nearby Kinston.

After graduating from high school, she enrolled in Flora MacDonald College in Red Springs, North Carolina.

Bailey joined the Women's Army Auxiliary Corps (later the Women's Army Corps) at Fort Bragg, North Carolina, in the summer of 1942, and was sent to Officer Training School at Fort Des Moines, Iowa, where she was a member of third class of WAACs.

[citation needed] Bailey remained in the army after World War II and was sent to Miami, Florida, where she served as vocational guidance and counselor officer for veterans.

In 1957, she graduated from Strategic Intelligence School,[2] and then reported to Fort McPherson, Georgia, where she served as the head of recruiting for the Southeastern United States for three years.

As director, Bailey is remembered for designing the army's female drill sergeant hat in 1972.