The paintings were commissioned from Lely by James, Duke of York, brother of King Charles II, in late 1665. James had commanded the English fleet against the Dutch at the Battle of Lowestoft on 13 June 1665, and the portraits were intended to commemorate those who had served under him as junior flag officers and captains of some of the ships. Lely, Principal Painter to King Charles II, was working on the series known as the 'Windsor Beauties' at the time for James's wife, Anne Hyde, Duchess of York. The full set consists of thirteen portraits of admirals and senior officers, or 'Flaggmen' as they were known at the time.