Goltzius took great care over the execution of this portrait, devoting the skills he accumulated over thirty years as a portrait draughtsman to the task. First he made an outline drawing in fine red chalk, traces of which can be seen even in areas such as the collar and shoulders. The shape of the skull is also visible through the hair. Then he added the red and black chalk with clear, decisive strokes, working the two chalks together in places so that there appears to be a third colour, brown. Finally, he applied passages of red and black stump, using the side of the chalk or his fingers. In the forehead and cheeks in particular, this has been done with great delicacy.

The earliest coloured chalk drawing by Goltzius is the Head of Gillis van Breen, dating from 1588, which suggests he had access to Italian drawings even before his time in Rome. But it is mostly after Goltzius’ trip to Italy, in 1590-91, that he turned to the softer medium of chalk and largely abandoned silverpoint and portrait engravings. This transition concords with the development of his portraiture, his images becoming larger and freer with the passing of the time. Here, the influence of Federico Zuccaro’s red and black chalk drawings is evident, and perhaps those of Federico Barocci, who was in Rome at the same time as Goltzius himself.

Goltzius commenced his career as a portraitist working in metalpoint at a time when no other Netherlandish artist was using such a medium. Portraits in different coloured chalks have few equivalents in the history of Dutch drawing. Reznicek suggested a date of around 1600 for our drawing on the basis of a photograph.

The traditional identification of the sitter as the young Jacob Matham seems unlikely given that Matham would have been nearly thirty years old at the time of this drawing.