Young Man Holding a Staff is one of only a handful of Pieter Claesz Soutman's surviving paintings, most of which date to the 1640s when he was working in his native Haarlem. In addition to the attractive young model with his expressive gaze and flowing golden locks, the painting's appeal also stems from Soutman's remarkably fresh and vigorous brushwork. Young Man Holding a Staff is a superb example of a tronie, or "character study," an important type of Dutch and Flemish painting that straddles the fields of genre painting and portraiture. The painting's excellent condition heightens the intensity and sense of immediacy of the image.

This painting provides a fascinating glimpse into the close connections that existed between the northern and the southern Netherlands, specifically between Haarlem and Antwerp. Soutman began his career as an engraver in Haarlem, presumably after training with Hendrick Goltzius. He moved to Antwerp around 1615 to make reproductive engravings of paintings by Peter Paul Rubens. While in Rubens's workshop, Soutman also started to paint, and his work clearly shows the influence of the elegant style of Anthony van Dyck, Rubens's most important assistant.

In 1619, Soutman became a citizen of Antwerp and joined the artists' Guild of Saint Luke. Probably on the recommendations of Rubens and young Prince Władysław of Poland, who visited Rubens's studio in 1624, Soutman served as court painter to King Sigismund III Vasa in Warsaw from 1624 until 1628. He returned to Haarlem in 1628, where, in 1633, he married and joined that city's Guild of Saint Luke. Soutman painted this evocative tronie in 1640 in a style that recalls Van Dyck's figure studies, an indication of the strong appeal of Flemish art in Haarlem at that time. During the 1640s Soutman received a number of important portrait commissions, including ones from Haarlem militia companies. At the end of the decade Constantijn Huygens, secretary to Prince Frederick Hendrick, invited Soutman to participate in the decoration of the Oranjezaal in the Huis ten Bosch, which remains an official residence of the Dutch royal family.