A remarkable series of pen, ink, and watercolor drawings of the London aldermen during the mayoralty of Sir John Olney (1446-47) have been attributed to Roger Leigh, Clarenceux King of Arms (d. 1460). The portraits are probably not accurate since the faces and clothing of the 25 aldermen varied little; instead, the focus is on the alderman’s heraldic arms, as displayed on the shield he holds in his right hand. A scroll floating above his head identifies each alderman, who rests his left hand on a large board that displays the names of previous aldermen of his ward. The portraits, some of them unfinished, were perhaps made to hang in the newly constructed London Guildhall. They have had several past owners, but are now held in the London Metropolitan Archives.

Since there are so few contemporary depictions of the church, civic, commercial, and domestic buildings of medieval London, scholars have turned to sixteenth- and seventeenth-century drawings and engravings of buildings known to have existed in the medieval period to understand the architectural features of these buildings.

Detail from The Canterbury Tales depicting Geoffrey Chaucer (c. 1340-1400) taken from the Ellesmere Chaucer, a highly decorated deluxe manuscript completed c. 1400-1410. The manuscript contains 22 minature paintings of the pilgrims who travelled in a group from Southwark to the shrine of St Thomas Beckett in Canterbury. The Canterbury Tales consists of the stories they each told along the way. The manuscript was for three hundred years in the possession of Sir Thomas Egerton (later Baron Ellesmere) and his family.