What did Anne Boleyn look like? The honest answer is: we’re not sure. No confirmed lifetime portrait of Anne survives — after her execution in 1536, Henry VIII ordered her images destroyed. What we have are ambassador reports, a debated portrait type, and a single medal.
The Venetian ambassador described her as “not one of the handsomest women in the world; she is of middling stature, swarthy complexion, long neck, wide mouth, bosom not much raised.” The imperial ambassador Eustace Chapuys, who was hostile to her, was less generous. The papal nuncio noted her “beautiful black eyes.” Multiple sources agree on dark colouring — dark hair, olive or “swarthy” complexion, and dark eyes — which was unusual at the English court, where the beauty ideal favoured fair skin and light hair.
The NPG portrait (National Portrait Gallery 668) is the best-known image, showing a woman with an elongated face, high forehead, pointed chin, dark hair worn under a French hood, and a “B” pearl necklace. But this painting dates from the late 16th century and is likely a copy of a copy. The “Moost Happi” medal, struck c. 1534, may be the closest we have to a contemporary likeness: it shows a woman in profile with a long nose, small mouth, and pointed chin under a gable hood. Her famous alleged sixth finger and neck mole are almost certainly later myths — no contemporary source mentions them, and the Catholic propagandist Nicholas Sander introduced these details decades after her death to paint her as a witch.