Nicholas Hilliard was a young goldsmith when in 1571 he produced a ‟booke of portraitures‟ for Robert Dudley, Earl of Leicester. 1571 was also the year of Hilliard’s first known work as a ‟limner“ or painter of portrait miniatures. Leicester was one of the earliest patrons of the young artist and may have introduced him to court.
Hilliard would paint Leicester many times, and the earliest surviving portrait miniature (now in the Victoria & Albert Museum) of the earl was painted sometime between 1571 and 1574, when Leicester would have been around 40. It seems likely that Leicester sent the picture as a gift to his sister, Mary, Lady Sidney.
Elizabeth Goldring, Robert Dudley, Earl of Leicester, and the World of Elizabethan Art: Painting and Patronage at the Court of Elizabeth I, 2014.
Alan Haynes, The White Bear: The Elizabethan Earl of Leicester, 1987.
Karen Hearn, Dynasties: Painting in Tudor and Jacobean England 1530–1630, 1995.