A portrait drawing of Anne Boleyn (c.1500-1536) on pink prepared paper. She is shown bust length in profile facing to the left. She wears a fur collar and linen cap. The drawing is executed entirely in black and coloured chalks.

An eighteenth-century inscription (a copy of a mid-sixteenth-century original) at top left identifies the sitter as 'Anna Bollein Queen.'. 

Although the identification of the sitter has been doubted, her informal dress and the presence of an inscription based on an identification made by Sir John Cheke have been cited as convincing evidence that the sitter is the queen (see, for example, John Rowlands and David Starkey in the Burlington Magazine, February 1983, pp. 90-2). Attention has also been drawn to the nightgown worn by the sitter, which may be identifiable as one given to Anne by Henry VIII (see Maria Hayward, Dress at the Court of King Henry VIII, 2007, p. 169). Abrasion has removed some pigment from the sitter's hair meaning that it may now appear lighter than it did when the drawing was made. The sitter's eyes are brown.

Anne Boleyn was the niece of Thomas Howard, Duke of Norfolk. She married Henry VIII as his second wife in 1533. In the same year, their daughter Princess Elizabeth (later Elizabeth I) was born. She was executed on spurious charges of adultery on 19 May 1536.

This is the only Holbein drawing in the Royal Collection which also has work on the verso. This is a sketch of the Wyatt arms and supporters. There is nothing to suggest that this has any connection with the portrait drawing. It may be that the sheet was reused as a spare piece of paper after Anne Boleyn's fall. It may not be a coincidence that Henry Wyatt, who was painted by Holbein, died in November 1536, a few months after Anne's execution and at exactly the time we might expect the sheet to be reused. Could the Wyatt arms on the verso be associated with his funeral, or with the chantry chapel he had founded for his commemeoration at Milton in Kent?