Philip the Handsome was so called because of his fair hair and attractive grey-blue eyes. He was the only surviving son of the Holy Roman Emperor Maximilian I and Mary of Burgundy (daughter of Charles the Bold of Burgundy and granddaughter of Philip the Good). On the death of his mother in 1482 he took over the inheritance of the Netherlands, with his father acting as Regent until 1494. In 1496 he married Joanna of Castile (Catherine of Aragon's younger sister, known as Joanna the Mad for her erratic and violent behaviour) and briefly enjoyed the title of King Philip I of Castile.

This painting is considered one of the best contemporary versions of the much-repeated design. The original may have been intended to face a companion portrait of Joanna. This portrait lacks the immediacy of an image painted from life and is unlikely to be a faithful representation of the sitter's features. His black cap is worn low, pulled down over his forehead. In other versions, such as that attributed to the Master of the Legend of the Magdalene, the cap is adorned with a brooch depicting the Coronation of the Virgin. The Royal Collection version has no brooch. Philip is shown wearing a velvet cloth of gold lined with brown fur. Around his neck over a white tunic he wears the collar of the Order of the Golden Fleece.

This portrait may be dated to c.1500 by the age of the sitter (who would have been 22 at the time) and by comparison with other portraits, such as the two wings of the altarpiece showing Philip and Joanna of c.1505 in the Royal Museum of Fine Arts, Brussels.

The painting appears in Pyne's illustrated 'Royal Residences' of 1819, hanging in The Old Drawing Room at Kensington Palace (RCIN 922153).

Catalogue entry adapted from Bruegel to Rubens: Masters of Flemish Painting, London, 2007