Henry Pickering was a fashionable and talented portraitist who was much in demand after returning from Italy in 1740. His style echoes the prevailing portraitist of the day Thomas Hudson although Pickering can achieve a sense of endearing charm with his images of children that is difficult to equal. This particular portrait depicts a boy in perhaps his early teenage years dressed in the fashionable attire of the day, striking the popular adult pose of tricorn hat tucked beneath one arm and hand slipped within the waistcoat. Pickering seems to have travelled widely across the British Isles seeking commissions finally settling in Manchester in 1759. From the apparent style of dress this portrait would seem to date to about 1750 and shows all the hallmarks of his work despite compositionally being unusual for him.