This painting is one of the most enigmatic sixteenth century portraits in the Royal Collection.

It is a visually arresting image: painted full-length, nearly two metres tall, the man is silhouetted against an apparently imaginary landscape with the suggestion of buildings and ruins on the left and curious rock formations on the right.

Sixteenth-century portraits showing a sitter dressed entirely in one bright colour (rather than all black) are rare at this date, as are full-length portraits showing the figure in an outdoor setting.

On the basis of style the artist is thought to have been German or Netherlandish, possibly working in England. Artists associated with the painting in earlier inventories were Hans Holbein the Younger (1497/8-1543) and William Scrots (active 1537–53), but both are now thought to be unlikely.

The portrait was sold to Charles II in 1660 when he was at Breda as a portrait of the young Henry VIII by Holbein. The man’s pose, legs apart and hand on hip, is reminiscent of Holbein’s portrayal of Henry VIII. First recorded in the Royal Collection c.1666 – 7, the portrait was unattributed and described as ‘A young man in a red garment, red bonnet and white feather with his hand on his sworde and a dagger hanging by’.

During the twentieth century the painting was hung at Hampton Court, before that at Windsor Castle and Somerset House.

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