The subject became a Knight of Malta just over a decade before this portrait was produced. He successfully fought against the Ottoman Turks in 1565 but was only a mid-ranking officer who might not be considered an obvious subject for El Greco. He is believed to have been well connected, however, and in 1575 he was promoted to sergeant major, with the portrait possibly being made alongside this achievement. El Greco had not often worked on military portraits, and so this piece differs from his main body of work. He also tended not to produce full length works but for the purpose of this theme, it made absolute sense. Military related portraits tend to seek an atmosphere of strength and confidence within their subjects, and this specialist genre has attracted many of the great artists from past centuries. El Greco made many portraits during his lifetime but rarely of serving officers, and so this portrait of Vincenzo Anastagi certainly offers something different to his career.

The artist is believed to have been living in Rome at the time of this artwork. It would be just a little later that he relocated to Spain after receiving a considerable commissioned series which he could not turn down. El Greco would spend many years living in Spain from that point onwards and it undeniably influenced his artistic style which became more expressive. El Greco found portraits could be completed relatively quickly and fitted in between larger projects, helping him to finance his studio and avoid becoming too entrenched in his religious scenes for months on end. Additionally, there was the benefit of drawing in more patrons for these commissioned pieces, some of whom might return later with more profitable projects for the artist to take on.

The composition itself features Vincenzo Anastagi looking directly at us, with his hands on his hips. His clothing is beautifully delivered by the artist, with stunning armour and some ballooning trousers and long stockings. El Greco keeps the rest of the composition particularly simple, just with a few details of a room, allowing the full focus to be given to the subject himself. The model fills the full vertical space of the painting, and the layout is typical of Renaissance art, lacking some of the innovations which El Greco brought to the world in later decades. His life in Italy was an important period in his evolution, but he continued to develop after moving to Spain just a few years after this painting.