Wilkie was born in the village of Pitlessie in the parish of Cults, Fife. Here, he gazes straight out at the viewer, just as he would into the mirror to paint this striking self-portrait, made when he was twenty. He had by this time demonstrated his remarkable ability to portray contemporary events and with this work confirmed his skills as an accomplished portrait painter. Wilkie grips a portfolio in one hand and his pencil holder in the other. His fashionably tousled reddish hair and brown jacket stand out subtly from the similarly toned background. He may have painted the work just before his move from Edinburgh to London in 1805.