Between 1910 and 1914, Sickert made many two-figure genre scenes in Camden Town that are among his best-known work. Several including Ennui and Jack Ashore were studied from life in his room—a first-floor front—on the corner of Granby Street and the Hampstead Road. He referred to this address as Wellington House Academy after a school that operated from the premises in the early nineteenth century. Charles Dickens had been a day scholar there and based some of David Copperfield on his experiences at the school, which fired Sickert’s interest.

The title and subject of Jack Ashore evoke the shore leave of a sailor seeking female company. Like Ennui, Jack Ashore depicts Marie Hayes and Hubby. The composition was studied in this work and four other drawings, the scale of which are uniform without exception—roughly 35 by 25 centimetres or 14 by 10 inches—and these dimensions are 1:1 scale with both the large etching plate and the sole related painting, which were made around the same time. None of the drawings are squared for transfer and the replication of the composition was likely achieved by tracing. The related painting (Pallant House Gallery, Chichester) is not an exact scale replica of the drawings, however, as the subject was enlarged: the man’s head and the woman’s foot are cropped and details of the surroundings are omitted.

This drawing was made using a variety of graphic media. Sickert apparently began by making a drawing in black chalk. He then overworked it with pen and sepia ink. The pen lines were mostly applied in uniform diagonal hatching, which enhances the underlying distribution of shadow and half-tones. A touch of white heightening creates a gleam at the surface of the dressing-table mirror, which appears in several other pictures of Wellington House Academy.