A half-length portrait to right, looking forward to meet the gaze of the viewer. The sitter wears a brown jacket with a velvet collar against a plain background. His left arm rests on the back of the couch or chair in which he is sitting while his right hand, holding a porte-crayon, is partly tucked into his jacket.

Stanfield had an early career as a seaman before becoming a celebrated painter of theatrical scenery and moving dioramas, and subsequently the leading marine artist of his time after Turner. He first exhibited at the Royal Academy in 1820 and this portrait was commissioned by his early patron, George Watson Taylor MP. It was exhibited at the Royal Academy in 1829, the year of Stanfield's Presidency of the Society of British Artists, and may have been intended to commemorate this. In 1844, Stanfield became the first Honorary Curator of Pictures at Greenwich Hospital, looking after the works that form the core of the art collection of the National Maritime Museum.

The artist, John Simpson, was an assistant to Sir Thomas Lawrence and was a personal friend of Stanfield. Another different portrait by him of about the same date remains with Stanfield's descendants and a third, attributed, of about 1833, is in the National Portrait Gallery. This example, although relined, is known to be dated 1829 on the back of the original canvas and was engraved in mezzotint by William Say in 1834. Simpson and Stanfield may also have been connected through Captain Peter Heywood, who was one of the latter’s early patrons and whom Simpson painted in 1822 (BHC2766).

The painting was presented to the Museum in 1978 by a London dealer, the late Monty Bernard of Ryder Street, who had held it in his unframed stock since at least 1948.