By the early 17th century the Seyliard family was one of the oldest and most established in Kent owning lands in Chiddingstone, Hever, Brasted and Edenbridge. Variously spelt over the years Sylyard, Seylyiard, and finally Seyliard they became an increasingly large and important family from about a hundred years after the Norman Conquest through to the age of the Hanoverian succession. An old listing in the Witt Library, Courtauld Institute, London attributes this painting to John de Critz and states the sitter as being ‘Sr. John Sylyard’. The dates do not fit for it to be this member of the family but they do correspond with those given for Sir Thomas Seyliard, of Chiddingstone in Kent. The sitter was the eldest child of William Seyliard (1556-1595) and Dorothy (1562-1613), daughter of William Cromer. Born probably at Edenbridge in Kent at one of the family estates Thomas married in 1609 Elizabeth Beaumont (1580-1640) and had thirteen children, some of whom appear to have perished almost at birth.

Whilst owner of the manor of Chiddingstone Burghesh evidence suggests that Thomas and his family gained only the lands and actually lived in another property belonging to the Seyliards nearby. By the 12th century six manors were built around Chiddingstone, the oldest, Rendesley manor, being owned by Peter de Chiddingstone. Upon his death sometime before 1300 he left this manor to his two daughters who proceeded to divide the estate in two, forming the manors of Chiddingstone Burghesh and Chiddingstone Cobham. It is recorded that the Burghesh family settled well in the area, but by 1591 their moated manor house was a ruin due to neglect.

Family details are sketchy so it cannot be ascertained when Thomas was knighted and for what reason but his eldest son John was created a baronet in 1661, shortly after the Restoration of Charles II, implying a loyalty to the crown.

John de Critz (c.1551-1642) was one of a number of painters of Flemish and Dutch origin active at the English royal court during the reigns of James I and Charles I. He held the post of Serjeant Painter to the king from 1605 and as such his was a style taken up by many young painters in England at the time. Echoing de Critz and the late 16th century portrait style, this painting displays the melancholic influence so appreciated by late Elizabethan and Jacobean society. The sombre clothes and sensitively rendered face displays a marked turn in approach to portraiture with people at this time beginning to be recorded as human beings with psychological moods as against the icons of an earlier period. Stemming from renaissance Italy the cultivation of a melancholic humour indicated a certain intellectual prowess in scholarship, philosophy and poetry with Robert Burton even claiming that it contributed to being witty (Anatomy of Melancholy, 1621). It is worth noting however that Sir Thomas’s mother actually died the year this portrait was painted (1613) so the melancholic air need not necessarily be totally stylistic in this instance.