In 1532 a Venetian ambassador to the court of Henry VIII described Anne Boleyn as “not one of the handsomest women in the world. She is of middling stature, with a swarthy complexion, long neck, wide mouth, bosom not much raised, and in fact has nothing but the King’s great appetite, and her eyes, which are black and beautiful.”
It is true that Anne was never praised as a great beauty, but it was not so much her outward appearance which made the King fall for her. Anne had a remarkable wit. She was well educated and had honed her skills of flirtation and charm during her time at the French court.In the generations following her death, Anne was romantically portrayed as a raven haired vixen with smoldering black eyes. While her eyes were dark and quite striking, Anne’s hair was more likely a lighter shade of brown (some theorize that she may even have been a redhead) and, although only one contemporary image of her survives, her face was probably not considered the most beautiful in England.
Personally, I am of the opinion that Anne was not altogether what we would call “ugly” but rather that she did not fit with the beauty standards of Tudor England. She had olive skin, dark eyes, and was very slender with a small bosom. The Tudors preferred women to be of fair complexion and buxom of figure. Regardless of whether or not she met the criteria for the ideal Tudor lady, it was still ultimately Anne Boleyn’s mind and not her face that made her so extraordinary.