Lady Dorothy Sidney, later Countess Leicester, was a member of the Jacobean court and wife of Robert Sidney, the 2nd Earl of Leicester. This marriage was not a traditional one in the sense that her and Robert had wed in secret, much to the shock of those around them, and no one was to find out for a year. It also led to a family quarrel, despite connecting two powerful families, as Robert’s brother had married Dorothy’s sister, Lucy, and was clearly not comfortable with this new arrangement. This had not soured the relationship between Dorothy and her sister, as can be seen in the 1638 double portrait of Dorothy and Lucy by Van Dyck. In this portrait, as in the present example, Dorothy is depicted with flowers, both in her hair and in her lap.

A question arises as to why Dorothy seems to have been depicted with flowers so consistently. There are a few possible suggestions to why this is. It is possible that she was simply associated with flowers like these, however, this is quite unlikely given that these portraits were created at different times of her life. Another explanation would be allegorical- that Dorothy is depicted here in the guise of Flora, the Roman goddess of flowers and spring, whose Greek Counterpart is Chloris. Naturally, the iconography of these goddesses usually features flowers, which matches the present miniature. Furthermore, in Roman mythology, Flora was one of the goddesses of fertility, and of youth. This is particularly fitting for our sitter, who, in her short life of 44 years, had twelve children. Another depiction thought to be of Dorothy, by Oliver, was sold in 2013, and depicts her holding a sprig of rosemary, similarly a symbol of love, remembrance, fidelity, and loyalty.

Just why Dorothy would have been depicted as a goddess, however, requires further explanation. Oliver is known to have depicted many sitters ‘costume’ like this, including a portrait of an unknown woman at the V&A, and a young lady in costume at the Rijksmuseum. Both of these sitters are in ‘Masque’ costume. At the Jacobean court, Masque played an important role. Both Queen Anne and King James I had enjoyed participating in these theatrical shows, many of which were designed by renowned architect Inigo Jones. Though no evidence has yet been found to place Dorothy within one of these shows, it is possible that she is being depicted here as part of a wider trend of women being depicted wearing masque dress. Dorothy’s daughter, also Dorothy (and known as Dolly, 1617-1684) had been involved in one of these performances, of Luminalia: The Queen’s Festival of Light, in 1638 , so, this was not something that would have been completely alien to our sitter.

Isaac Oliver, being Queen Anne’s limner, would have at least been aware of, if not involved in, these masques. The miniaturist had trained under Nicholas Hilliard, but in his own work diverted away from the more traditional style that his master had encouraged. This is something that is especially reflected in the present miniature, given the fact that Dorothy wears a relatively low-cut dress and is wearing such a costume. The sitter’s family had been closely connected to both Oliver and his master, Dorothy’s father having been painted in an unusual miniature form, laid on grass, by Hilliard in c.1594-1595, in the Rijksmuseum, Amsterdam . The Essex family were patrons of the artist and Catharine MacLeod has talked about the influence that the artist had on the iconography of the family. Here, it can be seen that this was an influence that carried on into the next generation.