The son of a school headmaster, Robert Reid attended Phillips Academy at Andover. In 1880, he entered the School of the Boston Museum of the Fine Arts, where he studied under Otto Grundmann and Frank Crowninshield. The following year, he became an assistant instructor at the school, while in 1882, he was appointed editor of their publication, Art Student. Reid formed several of his most important friendships with other students, including those with Frank Weston Benson, Edmund Charles Tarbell and Willard Metcalf.
In 1885, Reid enrolled briefly at the New York Art Students' League, after which time he began a four year residence in Europe. In Paris, he attended the Academie Julian under Jules Joseph Lefebvre and Gustave Boulanger. Reid rented a summer residence and studio in Etaples-pas-de-Calais, where Monet had painted, from 1886 to 1889. In 1887, he spent ten months in Italy.
Following his return in 1889, Reid settled in New York. He taught at several institutions, including the Art Student's League from 1893 to 1896, as well as the Cooper Union. Along with Tarbell, and Benson, Reid was a founding member of The Ten American Artists, a group organized in 1897. His paintings of figures in brilliant sunlight from this time are closest to the American Impressionist style associated with The Ten.
Beginning in the 1890s, Reid became active as a muralist. His mural commission for the dome of the Liberal Arts Building of the World's Columbian Exposition, held in Chicago in 1893 was followed by commissions for the Library of Congress in 1897 and the New York Appellate Court House in 1899. In 1900, Reid painted a mural for the United States Pavilion at the Paris Exposition. He also designed a group of stained glass windows for the H. H. Rogers Memorial Church in Fairhavewn, Massachusetts, from 1901 to 1905. The influence of Art Nouveau becomes increasingly evident in Reid's large-scale mural architectural decorations, and in his his subsequent depictions of young women in floral environment for which he is best known.
Reid married one of his models, Elizabeth Reeves, in 1907. Ten years later, the couple settled in Colorado Springs, Colorado, where Reid was a founder of the Broadmoor Art Academy. During this period he depended upon portrait commissions for his livelihood. Reid called these works "portrait impressions," executing them in a rapid technique which resembles drawing in color. After contracting polio in 1926, the artist's right side was paralyzed. Reid entered a sanatorium in Clifton Springs, New Jersey, where he taught himself to paint with his left hand. He remained there until his death.
