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Simon Bening's mother was a close relative of Hugo van der Goes and his father Sanders Bening was an illuminator from Ghent, often active in Bruges. As a miniaturist, Simon himself was very representative of the grand late fifteenth-century Bruges tradition issued from Gerard David. He probably executed this miniature in 1535-36. At that date this type of half-length three-quarter portrayal, with a direct gaze and eloquent hands placed on the edge of the frame, had already become commonplace in the Lowlands through the paintings of Gossaert, Joos van Cleve, Jan Vermeyen and Jan van Scorel. The landscape background offers a modern version of what Memling had offered in the background of his portraits a century before. Without any clear evidence, the painting is believed to be a self-portrait.
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