Although she is best known for her oil portraits, Polly Thayer also painted landscapes and still lifes, and she worked in other media, including watercolor, pastel, and lithography. Born to a wealthy Boston family, she was once described as "one of the Back Bay's foremost society girls." She began her career with traditional training at the School of the Museum of Fine Arts and then privately with Philip Hale and with Charles W. Hawthorne in the late 1920s. Thayer achieved early success in 1929 when she won the National Academy of Design's coveted Julius Hallgarten Prize, given to an American artist under the age of thirty-five, for her large painting of a nude, "Circles" (New Britain Museum of American Art).
By the 1930s, Thayer expressed an interest in looking "into this thing called modernism," and toward that end studied with abstract painter Hans Hofmann in Provincetown during the summer of 1933. Her subsequent work is striking for its flattened pictorial space and vibrant color. "Cabbages," completed in 1936, illuminates her enthusiasm for this new way of painting. Her composition is filled with brilliant color-deep purple and green-and vivid contrasts of texture-tight whorls of glossy fresh leaves next to the flaccid draped forms of blemished ones. Thayer mentioned the painting in a letter to her friend the poet May Sarton (whose portrait she also painted that year), noting that "the cabbages are turning out well. They show a bit of temperament for a change…Could you write a poem about 'spare us the beauty of cabbages' or is the word unusable even in this day and age of poetry?" ("Poetry of Hand & Spirit: Paintings and Drawings by Polly Thayer (Starr)," exhibition catalogue, Boston: Vose Galleries, 2001, p. 16). When Thayer exhibited her new modern works, one Boston critic was forced to conclude that "at present it is difficult to trace [Thayer's] artistic genealogy to the Museum School, for in the last few years she has made a decided departure from accustomed methods." (Dorothy Adlow, "At Grace Horne Galleries," unidentified clipping, January 30, 1940, curatorial files, Museum of Fine Arts, Boston).