The son of educators Robert and Mabel Hughes Boulware, Harold Boulware attended Johnson C. Smith and Howard University Law School. After graduation he returned to South Carolina and established a legal practice in 1940. A year later, he became chief counsel for the South Carolina NAACP.
It was through Boulware's guidance that many civil rights victories were won for African-Americans in South Carolina. These included obtaining equal pay for African-American teachers and the Briggs v. Elliott desegregation case in Clarendon County.
From 1969-1974, he served as Associate Judge of Columbia's Municipal Court. He was the first African-American appointed to that position. In 1974, he became a judge for Richland County. His court later became the Family Court of the Fifth Judicial Circuit of South Carolina.