In his later life he primarily designed in Massachusetts and worked on many civic and community projects in Boston, in the town of Dennis, and in the surrounding area.
[1] Boles graduated with a B.Arch (1943) from Illinois Institute of Technology, where he studied under Ludwig Mies van der Rohe.
[1][2] From 1929 until 1943, while in school, Boles worked as a clerk for the United States Postal Service to support his family.
[1] After graduation he served for two years as an assistant plant engineer at the Aero Parts Manufacturing Company in Wichita, during the end of World War II.
[1][3] Early commissioned projects were the Methuen Junior High School and Saint Stephan's Episcopal Church Parish Hall (1961) in the Roxbury neighborhood of Boston.
[2] He was a member of the American Institute of Architects (AIA) and the National Association for the Advancement of Colored People (NAACP).