Long acknowledged as one of Van Dyck’s greatest works and one of the finest portraits to survive from his second Antwerp period (1627–1632), this work demonstrates the artist’s ability to capture not only his sitters’s likenesses but their aspirations. Philippe Le Roy (1596–1679) was the illegitimate grandson of a successful Antwerp manufacturer. As a result of his own financial acumen, Philippe was able to acquire the land and feudal rights to the villages of Ravels and Eel, and the right to call himself ‘Lord of Ravels’. In 1631 he married Marie de Raet (1614–1662), the daughter of François de Raet, almoner of Antwerp, Lord of Couwenstyn. He marked this union by commissioning the present pair of portraits from Van Dyck. Le Roy’s portrait was painted, probably to celebrate his betrothal, in 1630.