A double portrait depicting Holles on the left, and Holmes on the right. Holles is painted three-quarter length, to the right, in a brown silk garment with red silk drapery round his shoulders. He wears a dark brown full-bottomed wig and his right arm, which carries a sword of Oriental rather than English appearance, is bare to the elbow. Holmes is posed three-quarter length to the left in a brown silk coat, ample shirt showing from the elbows and his left arm leaning on a gun barrel. He wears his own hair and a brown silk turban with jewels in it. He stands in front of a column and points with a commander's baton in his right hand towards a sea fight depicted in the background. The date of the portrait of Holles, in particular, is uncertain.

In March 1672, he and Holmes sailed from Portsmouth and attacked the homeward-bound Dutch Smyrna convoy in the English Channel. This officially sanctioned foray precipitated the Third Dutch War in which Holles was very soon killed in command of the 'Cambridge', 70 guns, at the Battle of Solebay on 28 May 1672. The 'Turkish' dress of both sitters and the sea fight beyond make it likely that the painting commemorates the convoy attack. However, unless Holles sat to Lely between March and May, his portrait has to be posthumous and based on a life sketch or another earlier painting. Holles's pose also neatly conceals the absence of his left arm, lost while commanding the 'Antelope', 60 guns, at the Four Days Fight in 1666 - although this apparently did not stop him playing the bagpipes rather well, according to Samuel Pepys. Holmes commanded the 'Defiance', 64 guns, at the Battle of Lowestoft in 1665 and in the following year he led a small expedition against Dutch shipping in the Vlie estuary, where he burnt two men-of-war, nearly 200 merchantmen and storehouses on the shore. The affair was known as 'Sir Robert Holmes, His Bonfire'.

Lely, a Dutchman who arrived in England in 1641 after the death of Van Dyck, soon became his successor as leading portraitist of the day. He worked for Charles I, continued to flourish under the Commonwealth and Protectorate, and after the Restoration of 1660 was appointed Principal Painter to Charles II. The portrait is signed 'Sr. Rob. Sr. Frech. Pinx. OPL'.