David Martin was first the pupil and then the principal assistant of Allan Ramsay, the leading Scottish portrait painter of the mid-eighteenth century. It was during Ramsay's second visit to Italy that Martin was able to make his own way there, in order to take Ramsay's drawings for display at the Academy of Saint Luke, Rome's principal art academy. Once in Italy, like many artists, he seems to have dabbled in picture dealing, bringing back an important old master painting, Correggio's Head of a Boy. 

This self-portrait was painted shortly after Martin's return to Scotland. It gives a sense of the growing personal and artistic confidence that eventually enabled him to establish his own successful portrait painting practice in Edinburgh.