Portrait of a gentleman, possibly Colonel Sir John Walkinshaw of Barrowfield (1676–1780)

Ramsay's 1742 portrait of a gentleman thought to be Colonel Sir John Walkinshaw of Barrowfield (1676-1780) belongs to his early Edinburgh and London period, when he was establishing himself as the foremost Scottish portrait painter of his generation. The Walkinshaw family were a Glasgow-area landed family with Jacobite sympathies — Sir John's daughter Clementina Walkinshaw became the companion of Prince Charles Edward Stuart — which gives any portrait of the family a political subtext in the highly charged atmosphere of pre-Jacobite Scotland. Ramsay himself maintained careful political neutrality despite his Scottish nationalist sympathies, and his ability to serve clients across the Jacobite-Hanoverian divide reflects his professional pragmatism. A 1742 date places this portrait just three years before the 1745 Rising.

Ramsay's 1742 work shows his early Edinburgh manner — influenced by his Neapolitan and Roman training under Solimena and Imperiali — that combined Mediterranean warmth in the flesh tones with the direct characterisation that his Scottish sitters expected. The costume of a gentleman in this period — typically a dark coat with carefully described buttons and lace at the cuffs — required precise material description without dominating the face.