George Bellows painted this portrait during the second summer he spent in Woodstock, New York. The following summer he would purchase land and build a house for his family. While at Woodstock, Bellows began producing large-scale, ambitious portraits such as Katherine Rosen, a portrait of the daughter of his friend and neighbor, the artist Charles Rosen. Like many of Bellows's sitters in the 1920s, Katherine posed in historical dress while seated in a late Victorian armchair. The portrait exhibits the hallmarks of the artist's portraiture from this period—sensuous brushwork, rich color, dramatic contrasts of dark and light, and an emphasis on the sitter's character.

Bellows based this portrait on a compositional system called Dynamic Symmetry, which utilized an intricate structure of interlocking angles and planes to construct compositions. Many American architects and artists, both traditional and abstract, were drawn to Dynamic Symmetry, partially as a means of addressing the new formal challenges presented by European Cubism. Bellows was also inspired by the portraiture of Thomas Eakins, such as Kathrin (1961.18.17). Bellows had admired Eakins's work at the Eakins memorial exhibition at the Metropolitan Museum of Art in New York in 1917.