Portrait of Simon George of Cornwall

Portrait of Simon George of Cornwall, painted around 1537 and now in the Städel Museum Frankfurt, is among Holbein's most formally inventive English portraits. The tondo format — round panel, unusual in English portraiture — frames the young Cornish gentleman within a circular composition that echoes the medal portrait tradition while George holds a pink (possibly a betrothal token). The inscription and the format suggest the portrait may have been made to mark an engagement or marriage. Holbein's adoption of the tondo format for a royal court portrait demonstrates his willingness to adapt Italian and medallic conventions to English tastes — combining the intimate format of a keepsake with the psychological authority of a full-scale portrait.

The sitter holds the carnation with delicate precision, while Holbein renders his features with characteristic analytical clarity. The green background provides a restful contrast to the dark costume.