Portraits were now strongly in vogue at Henry VIIIs court, to facilitate or celebrate marriage, to cement love affairs and to commemorate the worthy. Courtiers eager for their likenesses to be taken included a new generation of humanist writers such as Sir Thomas Elyot and the poets Sir Thomas Wyatt and the Earl of Surrey. However, Holbeins subjects also included Mrs Small, the wife of a City of London cloth merchant, as well as the Kings household servants. Imitation of the portraits seen on classical coins may have influenced the interest in profile portraits, while the new fashion for classical and Italian Renaissance literature may also have sparked a desire for decorative subject paintings.
As well as painting portraits in oil, large and small, Holbein began to make portrait miniatures using pigments mixed with gum on vellum: perfectly balanced half-length compositions on a diminutive scale, they probably had precious metal settings. For his preparatory portrait drawings Holbein now used pink primed paper which provided ready-made flesh tones, adding ink for precise detailing of contours and features with the pen and brush along with vivid painterly washes.