'A Portrait Group' was originally painted in 1933 and featured four pupils of Bellshill Academy near Glasgow, where Cowie taught until 1935. Cowie dramatically reworked the painting in about 1940 and changed almost every detail. Most notably, Cowie had portrayed a young girl in the foreground of the first version, but later changed her into a mature woman. The painting shows the linear form of realism that Cowie practised. There seems to be no psychological relationship between the sitters, as the artist often assembled large compositions from separate studies. He always began his portraits by painting an eye, believing that the eyes were the most intense and compelling part of the sitter.