Much is known about Michael Sittow's peripatetic career painting for princely patrons, but few securely attributed paintings survive. A painter's son, Sittow was in his third year of apprenticeship in Bruges by 1486. In 1492 he was in Spain working as court painter to Queen Isabella. Although he remained in Isabella's service until her death in 1504, he had left Spain by late 1502. He then spent some time in the Netherlands and worked at the Danish court and in his Estonian hometown of Tallinn. He may also have traveled to England. By 1518 he was back in Tallinn, whose artists' guild he had joined in 1507.
Sittow specialized in small devotional works and portraits, which often projected a melancholy mood. For Margaret of Austria, Sittow produced a type of precisely observed portrait in which his sitter wore contemporary dress, a halo, and a reserved demeanor indicating sainthood.
Manuscript illumination and Netherlandish painting of the 1400s influenced Sittow's style. He used translucent layers of paint to achieve highly refined and subdued color harmonies, combined with sensitivity to texture and light effects.