The Chesterfield portrait of Shakespeare is just one of many examples of representations of the playwright. The portrait was named by one of its previous owners, the Earl of Chesterfield. It was acquired by the Trust in 1967. It is perhaps the most Baroque of all paintings of Shakespeare; his head is clearly modelled on the Chandos Portrait (now in the National Portrait Gallery) including the characteristic earring in his left ear. 

George Vertue, when he saw the picture at the Halifax sale in 1739-1740, thought it had ‘a head new painted onto the posture, perhaps by Sykes’ (a painter working in the early Eighteenth Century). If Vertue was right, the painting was doubtless made (of someone else) in the 1660s and then altered to represent Shakespeare around 1700. During restoration in 1962 no evidence of any such change was found, however.

A notable feature of this portrait is the gesture Shakespeare is seen to be making with his left hand. It is a variation on "logos" gesture which originates as far back as ancient Western Asia, but is seen on large quantities of art work from ancient Greece and Rome. There are various interpretations of the meaning of the logos gesture but there is a general consensus that it was used by orator’s to express wonder, amazement and enlightenment, but perhaps also as a signal for silence in order for the speaker’s resonating words to be heard.