Reginald "Reggie" Fairfax Bolles was born on February 27, 1877 to Matthew Shepard Bolles Jr. and Hellen A. Bolles.

His grandfather, Matthew Shepard Bolles Sr. began his career in banking in 1824, and was one of the founders of the Boston Stock Exchange. With his two sons, Matthew S. Bolles Jr. and Richard F. Bolles, he ran Matthew Bolles & Company on 19 Kilby Street in Boston, Massachusetts.

Reginald was a 1900 Harvard Graduate, member of the Hasty Pudding Club, an avid polo player, prankster, and well known as a theatrical eccentric.

Reggie was also an accomplished painter and illustrator having many works featured on the covers of magazines in the early 20th century. He was known to be an eccentric character who was charming and generous and well loved by many in the Cotuit village in Barnstable, where he and his wife, Claudia eventually settled. He did not take an interest in banking, especially after his father died in 1902, and instead pursued his passion and interest in the arts, which were clearly his talents.

He often featured his neighbors in his works of art and his work can be found at the Cahoon Museum of American Art in Cotuit, Massachusetts.

Reginald married Claudia Elizabeth Libbey on February 6, 1912 with his brother Matthew Bolles as witness. Claudia's father, Charles Henry Libbey, stood as "Best Man" for the wedding and Rev. A.A. Berle officiated the wedding in East Milton, a suburb of Boston.

Claudia was previously married and had three sons from that marriage; however she did not have custody or contact with the children or her ex-husband or his family. Reginald never knew his wife's children. They were married for about 55 years until his death in 1967.

Reginald and Claudia are not known to have had any children of their own. They are buried with Claudia's parents in the Mosswood Cemetery in Cotuit, MA.

Source:
FindAGrave: Mosswood Cemetery, Cotuit, Massachusetts

Reginald Bolles was a prominent illustrator in the 1920s and 1930s who produced many magazine covers and calendar images, such as Collier's or Field & Stream.

Source:
Heritage Auctions