Henry, Prince of Wales was the elder son of James I and Anne of Denmark. He was a cultured and intelligent young man, interested in books, pictures and works of art, and was a talented sportsman. On his early death from typhoid fever at the age of only eighteen, his collections passed to his younger brother Charles I.

This portrait was painted by Van Dyck during his second visit to London twenty years after the Prince's death, presumably to form part of Charles I's royal family portrait gallery in the Cross Gallery at Somerset House. The artist based the head on a large miniature by Isaac Oliver in the collection of Charles I. He dressed him in a famous armour for field and tilt made at the Greenwich Royal Workshops under the direction of Jacob Halder, c. 1608 which is decorated with the emblems of the Union of the Crowns (RCIN 72831). Both these sources, the miniature and armour are still in the Royal Collection.

The figure seems to be wholly by Van Dyck, but the curtain, cloth and plumes in the background were probably painted by an assistant and may have been partly overpainted later.