The "Painter of Trees", Olive Holbert Chaffee, was born on January 9, 1886 in Woodville, Kentucky. She began her formal training in art with private lessons while still in high school. Later she studied with Chauncey Ryder and George Conroy in New York. Chaffee attended the Corcoran Art Gallery School and was later influenced by W. Humphrey Woolrych in St. Louis and W.A. Pratt in Denver.

Chaffee's first marriage was to William Gibson in Cairo, Illinois. In the 1920's she moved to St. Louis and in 1926 she married artist and architect, Roy O. Chaffee. It was at about this time that her career took off. Her landscape paintings were mostly of Missouri though many reflect her trips about the country. She did landscapes of the Green Mountains of Vermont; western Kentucky; St. Petersburg, Florida; Colorado, Wyoming and California. One painting, titled Missouri Vetch Field, hung in the Oval Office during the presidency of Harry S. Truman.

The artist's exhibitions include the Women's National Exposition in St. Louis (1926) -first landscape prize; National Arts Club; the Southern States Art League; Wacha Galleries, St. Louis; Gramercy Park Art Club Galleries, New York; Noonan-Kocian Galleries; St. Louis and Barn Gallery, St. Louis.

Olive Chaffee died April 9, 1980 in St. Louis, Missouri.

Source:
An Encyclopedia of Women Artists of the American West by Phil Kovinick and Marian Yoshiki-Kovinick

The following information is from David Boyd

I have coming to me these paintings that were painted by Olive Chaffee:

1. Three oils, which I believe were painted in the 1930's
2. A watercolor, which I haven't been able to date.
3. Two or three sketches on board, which I'm relatively confident she painted in the latter years of her life, probably the mid 70's. These were done in Lookout Mountain Alabama, where she had a summer cabin for many years. After she became too old to drive from St. Louis to the mountain
location (near Chattanooga, TN), my mother drove her to the mountains from time to time. I believe these were done at that time, and I don't know whether any was used to make a larger, more formal painting.

Born in Woodville, KY on Jan. 9, 1886. Olive Holbert began painting at age ten and studied privately while at Paducah High School. She later studied with Chauncey Ryder and George Conroy in NYC and at the CGA. Upon settling in St Louis in 1925, she wed artist Roy Chaffee. While based there, she made painting trips to California and in 1940 had a second home in Glendale. Trees were her main painting subject. She died in St. Louis, MO on April 9, 1980. Member: NAC; St Louis Women Artists; Southern States Art League. Exh: Women's Nat'l Expo (St Louis), 1926 (1st prize). In: Governor's Mansion & Public Library (Jefferson, MO).