Edward Grosvenor Bolles was born in Rosamond, Illinois on November 12, 1871. He married his first wife Harriet Ida Savage on April 17, 1895 in Morgan County, Illinois. They soon moved out to the Bay Area and Edward started working as a draftsman for established architect, Albert Sutton (1867–1923). He stayed with Sutton from 1896 through 1902.

Living on Alameda Island at first, the family later moved to Berkeley. They had four children, Lyman G., Carol G., John S. and Elizabeth H., all born in the East Bay. Prior to 1920, Edward & Ida were divorced and Edward married Ohio-born attorney Suzanne Vervin (1873–1934).

Edward Bolles obtained his own State architectural license (B333) in April 1903 and opened his own office. At times in his career he worked with architect Albert Schroepfer (1874–1965). For one year, 1911, they listed themselves in the business section of the City Directory as a partnership. They collaborated a lot that year and worked together again on projects in the late 1920's. For many years they both kept offices at 68 Post St.

Bolles liked to set back the entry to a house on one of its sides and that can be seen in an illustration from the June 1915 issue of Architect & Engineer magazine. It shows 2829 Pacific Avenue, built in 1914 from a Bolles design. Similar entries can also be seen on many of the houses in Ashbury Terrace, Sea Cliff and West Clay Park that Bolles designed for the S. A. Born Building Company. Schroepfer also worked at times for the company.

In common with other architects at the time, Bolles designed apartment buildings, hotels, office buildings, and a few retail stores as well as houses. His contributions to San Francisco architecture include the following: