The Chaucer Review: An Indexed Bibliography (Vols. 1-30)

Krochalis, Jeanne E. "Hoccleve's Chaucer Portrait." 21 (1986): 234-45.
Portraits of authors existed in classical times, and medieval manuscripts also included portraits of authors, but these portraits often did not reflect the physiognomy of the author. Indeed, scribes and authors have the same features. Hoccleve memorializes Chaucer in his Regement of Princes and, in so doing, equates him with the rich and holy who could afford to be memorialized in effigy or in verse.

McGregor, James H. "The Iconography of Chaucer in Hoccleve's De Regimine Principum and in the Troilus Frontispiece." 11 (1977): 338-50.
The picture of Chaucer in Hoccleve was created after his death and displays specific ideas of Chaucer's purpose for writing. The frontispiece for Troilus and Criseyde may have been painted during Chaucer's life, but there is no way to decide conclusively. Hoccleve presents Chaucer as a poet who has arrived at the end of poetry: he is also a philosopher. Chaucer is also a good counselor, so Hoccleve presents an abridged Melibee, but he distorts the sense so that Chaucer becomes a counselor to princes. The portrait of Chaucer Hoccleve presents, then, is designed to inspire the prince. Chaucer is also presented as the instructor to the prince in the frontispiece to Troilus and Criseyde. Both portraits present Chaucer in a nationalistic sense, suggesting that his most important role is that of presenting philosophy to the ruler, thereby encouraging peace.