Wearing his customary black clothing and high hat, with the Order of the Golden Fleece on his chest, the Monarch holds a rosary in his left hand, alluding to the institution of the Rosary Festival by Pope Gregory XIII. This festival was to take place annually on the first Sunday of October to commemorate the victory over the Turks at the battle of Lepanto on 7 October 1571 and the triumph of Catholic faith.

This portrait was made while Felipe II was married to his third wife, Isabel de Valois. Sofonisba Anguissola was one of the queen's ladies in waiting as well as her painting teacher.

In 1573, Anguissola changed the placement of the King's hand —it previously touched the Golden Fleece— in order to adapt it to the portrait of his fourth wife, Ana de Austria (P1284), with which it is paired.

This is one of the paintings removed from the Royal Collection and taken to the Napoleonic Museum in Paris. It entered the Prado Museum in 1827.