Born in Cork on 18th October 1766, James Penrose was one of four sons of Cooper and Elizabeth Penrose. While three of the sons remained bachelors, in 1794 James married Louisa Fitzgerald of of Cork Beg, on the East shore of Cork Harbour, and they subsequently settled in the village of Whitegate, close to her family home. James and Louisa had at least five daughters, one of whom, Frances
Anne, married George Gumbleton of Belgrove, in Cork Harbour, while his fifth daughter Gertrude in 1835 married James Taylor Ingham, a barrister in London.

James Penrose was one of the group of yachting enthusiasts, his father among them, who re-established the yacht club in Cork Harbour in 1806 He was also fond of hunting, and the Cork Evening Post of 24 March 1800 mentions his being granted a licence to kill game.

Like the Penrose family, the artist who painted this portrait of James was no stranger to controversy. Born in Dublin in 1769, Martin Archer Shee studied art at the Dublin Society´s Drawing Schools. He then moved to London, pursuing a successful career as a portrait painter. Shee was also a talented poet and playwright, and in the 1820´s his play Alasco was banned for advocating Republican principles.

This however did not prevent Shee´s election, in 1830, to the presidency of the Royal Academy. Shee´s portrait of James Penrose, painted around 1806, shows the young man dressed in classic Regency style, with ruffed lace collar and red velvet jacket. The painting depicts James as a dashing Byronic figure, rather than a conservative businessman, and this is in keeping with the perception of
the Penrose family in the city of Cork at that time.