The best-documented portion of John Wollaston’s life is the time he spent in the North American colonies. (For the most thorough discussion of Wollaston’s English background and early American career, see Wayne Craven, "John Wollaston in England and New York," in American Art Journal VII [November 1975], pp. 19–31.) There is general agreement that Wollaston’s father was a minor London painter named either John Wollaston, Sr. (alternatively spelled Woolaston), or perhaps T. Wollaston. The younger Wollaston may have apprenticed with a drapery painter. His style (notably his trademark “almond” eyes), indicates an awareness of the work of Thomas Hudson, a leading London society portraitist of the second quarter of the eighteenth century.
John Wollaston left behind a London studio and a modest career as a portraitist when he arrived in New York in 1749. Armed with the lighthearted rococo trappings of the latest London style, he was immediately embraced by a well-to-do provincial populace, a mix of merchants and landed gentry, who had money to spend, but limited opportunity to spend it in truly fashionable ways. The cream of New York society lined up to be painted by Wollaston. In three years in New York, Wollaston painted a who’s who of the colony in an upscale, uniformly rich, and cheerful mode. Wollaston took his palette and brushes south to Maryland (via Philadelphia) in 1752–53, making his base in Annapolis. From 1755 to 1757 he painted in Virginia, and in 1758 returned to Philadelphia. In 1759, Wollaston traveled to India to work as an administrator for the East India Company, where he served as a magistrate in Calcutta. He was back in New York by 1767, and in that year also painted about twenty portraits in Charleston, South Carolina. He soon returned to England, leaving in America a known body of at least 300 portraits. Wollaston was seen in London in 1775, the last documented mention of him.