Hans Holbein the Younger first sketched the sitter, whose identity is unknown, with black chalk. Subsequently, he used a brush and ink to describe the hair and collar. He used a pointed quill pen and ink to make the contour lines of the face and details such as the small dots that suggest the stubble of an incipient beard. In this second stage, Holbein made several changes in the outline of the hat and the cloak just behind the sitter's head. He used a soft red chalk over the pink ground of the paper to model the face subtly.
Holbein became painter to the court of King Henry VIII of England in 1536. After the artist's death in 1543, numerous drawings of members of the court were found in his studio. This group of drawings, which may have included this portrait, was gathered into the so-called "great booke" and given to Henry VIII.