The sitter was the daughter of Captain John Stirling (died 1756) of Auchyle and Herbertshire and Christian, daughter of Sir William Stirling, Bt. of Ardoch. Born in March 1722 she married firstly in January 1751 Sir James Stirling of Glorat, who died in April 1771. She later remarried the Honorable James Erskine of Alloa, later Lord Alva, a senator of the College of Justice. On the death of her father in 1756 the family estates passed firstly to her brother George and then at his death to her in 1760. As the primary representative of the Auchyle branch of the Stirlings, who had settled in the area in the 15th century, Jean would have been a wealthy and influential heiress and probably a fair match for her significant husbands. Along with the Auchyle estate she inherited Herbertshire Castle, a 15th century hunting Lodge that had once belonged to both the Dukes of Orkney and the Earls of Linlithgow, and from whom it passed to the Stirlings sometime in the 17th century, and was sold in 1768. Jean died a year after her husband in 1797, and, having had no children, the estates passed to her cousin Lieutenant-General Alexander Graham-Stirling (1769-1849) of nearby Duchray Castle.
Jean Stirling is depicted in this painting as a young child of just a few years, fashionably dressed in the Greco-Roman attire that was often deployed at this time. Artists embraced many of the attributes of the late baroque and together with a love of the developing Palladian style of the early 18th century drew inspirational, often poetic, visions. Set within a rocky, leafy, landscape, evocative of the arcadia of Inigo Jones, the small child exerts a presence that fails to be dominated by the splendour of the setting. Strikingly swathed in a reddish-pink toga, she reaches confidently towards the exotic parrot in the trees above her head; the rolling acres she is destined to one day inherit visible behind her through the break in the trees. Such evocations would have been truly appreciated by eager patrons, in this case the childs parents, who almost certainly would have commissioned this to hang in the main family home at Auchyle. The composition of this portrait closely resembles that by Sir Godfrey Kneller of Lord Euston painted in 1689.