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.

It is difficult to identify the nationality of the artist who painted the Man in Red. In this period artists travelled throughout Europe to work in different centres, the most famous example being Hans Holbein the Younger, who moved from Basel to London. One artist proposed for the Man in Red - Gerlach Flicke (active 1545 – 58) - originated in northwest Germany, was probably trained close to or in the neighbouring Netherlands and was active in London. Many Netherlandish artists were also working in England, for example William Scrots (active 1537 – 53), who worked in England from 1545. This work has previously been attributed to him, though his portraits are different stylistically and technically. No surviving portrait of this date painted in the Holy Roman Empire, France or the Netherlands closely resembles the Man in Red in format, style and technique. Taking into account all the evidence together with the assessment of the costume it seems that the sitter is more likely to be English and the portrait made in England. Analysis of comparable portraits has ruled out a French artist, but it is possible that the artist was German or Netherlandish working in England.

Identifying sitters in portraits painted more than 400 years ago is difficult because of the scarcity of records and comparable likenesses. Various candidates have been proposed for the Man in Red’s identity, although there is currently no conclusive answer. Facially he appears to be an adolescent, possibly in his late teens, with a beard just starting to grow. Evidence from the technical analysis and costume suggests that the painting was produced between c.1530 and c.1550. Assuming the sitter is aged between fifteen and twenty this would put his date of birth between c.1510 and c.1535.

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.

On the bottom half of his legs the sitter wears lower stocks, which might be made from woven woollen fabric, knitted silk or dyed deerskin. Above these are upper stocks, constructed from panes of alternating types of fabric, one woven with metal thread and the other probably crimson silk velvet. The two garments would have been laced together above the knee to make up the tailored hose. The fabric shoes are decorated with slashing and buttons. His linen shirt is decorated with foliate blackwork embroidery. The manner in which the clothing has been painted makes the exact combination of garments worn over the shirt hard to interpret. Normally a man would wear a doublet over his shirt, which would be laced to his hose at the waist. Although such a garment is not apparently visible here, it is possible that one with a very low neckline is being worn beneath the coat. This example has skirts below the waistline and is worn open down the front, evidently to display the fine embroidery on the shirt. The outermost layer is a gown reaching to mid-thigh with decorative aglets at the shoulders. It is not clear whether the fabric covering the forearm is part of the coat beneath or the gown. These lower sleeves are decorated with ‘pullings out’ – diaphanous fabric woven with gold thread is pulled through slashes in the layer above. Like most gowns at this date, this one appears to be of velvet. The sheen on the large collar, turned back to reveal the lining of the gown, suggests it is possibly lined with a fabric woven with metal thread. The most expensive fabrics were often reserved for linings.

The painting appears in Pyne's illustrated 'Royal Residences' of 1819, hanging as an overdoor in the Queen's Drawing Room at Windsor Castle (RCIN 922102).