Sir Anthony van Dyck was born in Antwerp in 1599 and originally trained with the Mannerist painter Hendrick van Balen (1575-1632). Between 1618 and 1620, while already a master, he worked as an assistant in the studio of Rubens, before seeking work in England with James I. His first stay there was brief, and he moved on to Italy in 1621 where he increasingly turned away from history painting to portraiture, especially in his portraits of the Genoese nobility.

In 1628 Van Dyck returned to Antwerp, where he remained until 1632 before travelling once again to England. This time he successfully captured the attention of Charles I, who appointed him his court painter. Van Dyck was responsible for creating a range of iconic images of the king and queen and their court, with a great sense of elegance and opulence. His enormous popularity and demand for his work necessitated a large workshop, which also produced copies of some of his portraits, especially of royalty, and Van Dyck was rewarded with a knighthood for his services. In 1639 he married Mary Ruthven, one of queen Henrietta Maria's ladies-in-waiting; the couple's daughter Justiniana was born on 1 December 1641, but Van Dyck died just over a week later on 9 December. He was buried in Old St Paul's Cathedral in London, where the king commissioned a monument to commemorate him; the tomb was destroyed with the cathedral in the Great Fire of London in 1666.

Van Dyck also painted religious subjects, but it is for his portraits that he is best known, in which he successfully lent an air of elegance, beauty and wealth to his sitters. In a way, he painted an idealised but enduring record of a court soon to be torn apart by Civil War. His influence as a portrait painter lasted well into the nineteenth century, with later artists such as Sir Joshua Reynolds and Thomas Gainsborough portraying their sitters in a 'Van Dyck' manner and costume, while his work also found many admirers and followers on the Continent.

Van Dyck painted several self-portraits, the first one around 1613-14 when he was only fourteen or fifteen years old (Vienna, Gemäldegalerie). A more sophisticated work is his bust-length self-portrait of about 1617-18 (Munich, Alte Pinakothek), which was painted while the artist was completing his training in Antwerp. This was followed by a half-length self-portrait (New York, Metropolitan Museum) possibly painted in the winter of 1620-21 during the artist's first stay in England. The Hermitage painting is essentially a variation of the two earlier versions, with the head at a similar angle, the artist again dressed in splendid dark silk with highlights of his white shirt underneath, and a strong emphasis on his elegant hands. This last version is, however, the most sophisticated and ambitious, and probably dates from 1622-23 when Van Dyck was either 23 or 24 and resident in Rome.

In the Hermitage self-portrait, Van Dyck painted himself as a handsome, elegant and confident young man leaning nonchalantly against a balustrade with a broken column on his right, suggesting a classical environment that would be in keeping with its having been painted in Rome. The artist's soft curly hair frames his face on either side, while he scrutinises the viewer; his black silk costume is only tied together at the front with a single bow and has slit sleeves, revealing the white shirt underneath. The right hand with its tapering fingers is hanging down from the balustrade, while the left arm is bent with the back of the hand against the artist's hip in a pose that Van Dyck was to use many times for his later portraits of Charles I and the English aristocracy.