There are a number of images that are associated with the English poet, Edmund Spenser (1552/4–99), most notably the so-called ‘Kinnoull’ and ‘Chesterfield’ portraits. This essay explores the question of identification of the surviving pictures linked to Spenser and asks whether he might have sat for a portrait or even commissioned one himself. The essay draws on new research of portraits of late sixteenth-century English writers of the ‘middling sort’. It examines the cultural and iconographic contexts of portraiture in the late sixteenth century in order to establish how the supposed portraits of Spenser can be compared to those of other Elizabethan citizens and writers. In tracing the desire to identity portraits of Spenser the authors explore the provenance and history of the surviving portraits. The supposed portraits were ‘discovered’ and identified as Spenser in the eighteenth century when there was a interest to present the writer within new editions of his printed works, which raises a number of awkward questions. The lack of correlation between of the supposed portraits of Spenser and authentic surviving portraits of other writers indicates that these portraits do not depict Spenser. The essay concludes by arguing that Spenser may never have commissioned a portrait, but that in any case the limited evidence about his appearance makes identification particularly difficult, creating opportunities – as with other writers of this period – for imaginative depictions.