The eleventh child of Maximilian II, Holy Roman Emperor and Maria of Spain, Archduke Wenceslaus of Austria spent his youth in the Spanish court of Philip II, who had married his sister, Ana of Austria. He moved to Madrid with his siblings in 1570, and must have sat to Sánchez Coello for this portrait shortly thereafter; it was presumably commissioned by Ana herself. Maria Kusche (op. cit.) dates the work to 1571-2, preceding therefore the signed and dated full-length portrait of 1574, showing Wenceslaus aged thirteen, which hangs together with its pendant, a portrait of his elder brother, Archduke Albert (1559-1621), in the Castle of Ambras, Innsbruck.
Sánchez Coello was one of the most renowned portraitists of his time. He served as a court painter to Philip II for over thirty years, from 1555 until 1588, continuing the tradition of Titian and Anthonis Mor (with whom he trained) in producing representations of the Habsburgs. Whilst relatively little is known of his studio practices, and a significant amount of his work was lost in the devastating fires at the Royal Palace of El Pardo in 1604 and the Royal Alcázar in 1734, his reputation as a highly skilled portraitist endures.