Bernaert van Orley's contemporaries called him the "Raphael of the Netherlands" for his interpretation of Italian Renaissance ideas and forms. His first encounter with such compositions occurred when Raphael's Vatican tapestry cartoons were woven in Brussels beginning in 1516.
Van Orley was probably taught by his father. By 1517 he was a leading designer for Brussels's thriving tapestry industry, master in the painter's guild, and head of a large workshop. In 1518 he became court painter to Margaret of Austria, for whom he provided mainly portraits, a position he retained under her successor.
Van Orley created a theater-like feeling in his paintings by assimilating Italianate architectural and figural motifs, inspired in part by Andrea Mantegna and Raphael's works. Around 1525 he shifted his attention to towards tapestry and stained-glass design, including windows for the Brussels Cathedral. His presentation drawings for tapestries, by far the most numerous surviving examples of his draftsmanship, depict the lineage of the House of Nassau, the Netherlands' royal family.