Daphne Charlton was a student at the Slade School of Art in London, as was Stanley Spencer, and her husband George taught there. The Charltons were introduced to Spencer in 1939 and from then on he often visited them at their Hampstead home. All three went on a painting holiday together in the summer of 1939 to Leonard Stanley, a remote village in Gloucestershire. During this stay Daphne Charlton painted Spencer's portrait. In April 1940, back in London, she sat for this portrait every day for about two to three weeks. The hat she wears was bought for three guineas in a shop in Bond Street in December 1939, especially for the sittings. Spencer painted another portrait of her without her hat.