Bailey was born January 11, 1882, in Kewanee, Illinois. After completing high school, he enrolled at the University of Illinois at Urbana-Champaign in 1900. He was the first African-American graduate of the University of Illinois’ School of Architecture with a bachelor of science in architectural engineering. He went on to earn an honorary master’s degree in architecture from the university in 1910.
After graduation, he worked for a small architectural firm owned by Harry Eckland in his hometown of Kewanee. During this time he also used to work for a Champaign, Illinois firm, Spencer & Temple. Bailey assisted in the planning of the 1905 Colonel Wolfe School.
In 1905, Bailey was appointed as the head of the Mechanical Industries Department at the Tuskegee Institute. While at the school, Bailey designed several campus buildings including White Hall (1908) and a girl’s dormitory. He remained at Tuskegee until 1916 when he moved to Memphis and opened a practice.
After Bailey’s move to Memphis, he began the first of multiple commissions for the Knights of Pythias. He designed the Mosaic State Temple Building and the Pythian Theater Building, both in Little Rock in 1922. The next year he undertook another Arkansas commission, this one in Hot Springs, the Pythian Bath House, and Sanitarium. Walter T. Bailey died on February 21, 1941, from pneumonia and complications caused by heart disease.