sad. She had painted the entire royal family and even the Pope commissioned Anguissola to do a portrait of the Queen. At the Spanish Court In 1558, already established as a painter, Anguissola went to Milan, where she painted the Duke of Alba, Fernando Álvarez de Toledo. He in turn recommended her to the Spanish king, Philip II. The following year, Anguissola was invited to join the Spanish Court, which was a turning point in her career. Anguissola was approximately 26 when she left Italy to join the Spanish court. In the winter of 1559–1560, she arrived in Madrid to serve as a court painter and lady-in-waiting to the new queen, Elisabeth of Valois, Philip's third wife, who was herself an amateur portraitist. Anguissola soon gained Elisabeth's admiration and confidence and spent the following years painting many official portraits for the court, including Philip II's sister, Joanna, and his son, Don Carlos. These types of painting were far more demanding than the informal portraits upon which Anguissola had based her early reputation, as it took a tremendous amount of time and energy to render the many intricate designs of the fine fabrics and elaborate jewelry associated with royal subjects. Yet despite the challenge, Anguissola's paintings of Elisabeth of Valois – and later of Anne of Austria, Philip II's fourth wife – were vibrant and full of life. During her 14-year residence, she guided the artistic development of Queen Elisabeth, and influenced the art made by her two daughters, Isabella Clara Eugenia and Catherine Michaela. Anguissola painted a portrait of the King's sister, Margaret of Parma, for Pope Pius IV in 1561 and, after Queen Elisabeth's death in childbirth in 1568, painted the likeness of Anne of Austria, Philip's fourth wife. While she continued painting portraits at the court, the Althorp Self-Portrait is the "only securely attributed work surviving from this period". For the royal family, Anguissola produced detailed scenes of their lives that now hang in the Prado Museum. With the gifts and a dowry of 12,000 scudi she earned along with her salary as court painter and lady-in-waiting to the queen, she amassed an admirable return from her craft. While in the service of Elizabeth of Valois, Anguissola worked closely with Alonso Sanchez Coello. So closely in fact, that the famous painting of the middle-aged King Philip II was long attributed to Coello or Juan Pantoja de la Cruz.