She transferred to the Woman"s College of the University of North Carolina (now The University of North Carolina at Greensboro) in her sophomore year and graduated in 1940. After graduation, she attended summer school at the University of North Carolina at Chapel Hill.
After graduating from high school, she enrolled in Flora McDonald College in Red Springs, North Carolina. Bailey went on to teach French in Taylorsville, North Carolina. Bailey was assigned to the United States Army Air Corps and stationed in Daytona Beach, Florida, until mid-1943, when the company she commanded was transferred to George Field Army Air Base in Illinois.
Bailey remained in the army after World World War II and was sent to Miami, Florida, where she served as vocational guidance and counselor officer for veterans.
In 1949, she was transferred to Stuttgart, Germany, with an intelligence assignment. She was then sent to Munich to command a Women's Army Corps attachment at the 98th General Hospital.
In 1953, Bailey returned stateside to Washington, District of Columbia, where she worked in the intelligence branch of the Military District of Washington headquarters. In 1957, she graduated from Strategic Intelligence School, and then reported to Fort McPherson, Georgia, where she served as the head of recruiting for the Southeastern United States for three years.
In 1961, she was put in charge of the Women's Army Corps detachment at Fort Myer, Virginia, the largest detachment in the United States. While there she worked on building a woman’s exhibit for a traveling set of exhibits that would inform the country about the army.
Bailey worked from 1963 to 1968 traveling with the tour and expanding the women"s history presentation. Upon returning to Washington, she worked as a liaison officer for the Senate. In 1970, she made deputy commander at the training center in Fort McClellan, Alabama.
On 2 August 1971 Bailey became the director of the Women"s Army Corps and was promoted to brigadier general.
She retired from the army in July 1975. Brigadier General Bailey died in Alexandria, Virginia on July 18, 2009 and was buried in Arlington National Cemetery.
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. Bailey was then sent to Walnut Ridge, Arkansas, for a short time before moving to Craig Air Force Base, Alabama, where she taught English to members of the French Air Force until the end of the war in 1945.