The sitter was the daughter of James Douglas, 2nd Marquess of Douglas (b.1646) and his second wife Lady Mary Ker, 3rd Daughter of Robert, 1st Marquess of Lothian. She married Colonel John Stewart, as his second wife, in 1746, who was later created a Baronet, as Sir John Stewart, of Grandtully, co. Perth, in 1759. Her brother Archibald Douglas, who succeeded her father as the 3rd Marquess of Douglas, was created Duke of Douglas in 1703. On the death of the sitter's brother in 1761, without issue, the Ducal honours became extinct, while the Marquessate devolved upon the Duke of Hamilton and the sitter's son Archibald Stewart was returned heir of line and provision to the late Duke. This outcome was disputed in the courts by the Duke of Hamilton on the grounds that Mr Stewart's birth was suspicious and the Scottish courts found in his favour but their decision was later overturned when an appeal was made to the house of Lords in 1769, a suit which attracted attention all over Europe. The sitter's son was afterwards entitled to the estates and assumed the title and arms of Douglas and was raised to the peerage as Baron Douglas, of Castle Douglas.
This portrait which is dated to circa 1735 is one of the earliest known portraits by the artist, and was included by Ingamells (op.cit.) as fig. 1 in his catalogue raisonne. Ramsay, who had shown proficiency as a draughtsman in Edinburgh had moved to London in 1732 to study under the Swedish born artist Hans Hysing (1678-1753), who was then at the height of his power as a portrait painter with a considerable reputation in royal and aristocratic circles. He returned to Edinburgh in the summer of 1733, where he initially set up as a portrait painter in his father's house on the High Street, and began to attract a fashionable clientele. This portrait is a very rare example of the artist's portraiture before he made his first visit to Italy (1736-38) which was to so profoundly affect his art, and shows the influence of Hysing. Other portraits of this early phase of his career include a three-quarter-length portrait of Mrs Margaret Calderwood, daughter of Sir James Stewart, 1st Bt. of Goodtrees, and wife of Thomas Calderwood, of Polton (Private Collection; Smart, op.cit., no. 71, fig. 3) and a three-quarter-length and a half-length portrait of Katherine Hamilton, younger daughter of Sir James Hall, 2nd Bt. of Dunglass (City Art Centre, Edinburgh and Private Collection; Smart, op.cit., nos. 237 and 238, figs. 4 and 5).