For Holbein, "everything began with a drawing".
A gifted draughtsman, he was heir to a German tradition of line drawing and precise preparatory design.
Holbein's chalk and ink portraits demonstrate his mastery of outline.
He always made preparatory portraits of his sitters, though many drawings survive for which no painted version is known, suggesting that some were drawn for their own sake.
Holbein produced relatively few portraits during his years in Basel.
Among these were his 1516 studies of Jakob and Dorothea Meyer, sketched, like many of his father's portrait drawings, in silverpoint and chalk.

Holbein painted most of his portraits during his two periods in England.
In the first, between 1526 and 1528, he used the technique of Jean Clouet for his preliminary studies, combining black and coloured chalks on unprimed paper.
In the second, from 1532 to his death, he drew on smaller sheets of pink-primed paper, adding pen and brushwork in ink to the chalk.
Judging by the three-hour sitting given to him by Christina of Denmark, Holbein could produce such portrait studies quickly.
Some scholars believe that he used a mechanical device to help him trace the contours of his subjects' faces.
Holbein paid less attention to facial tones in his later drawings, making fewer and more emphatic strokes, but they are never formulaic.
His grasp of spatial relationships ensures that each portrait, however sparely drawn, conveys the sitter's presence.

Holbein's painted portraits were closely founded on drawing.
Holbein transferred each drawn portrait study to the panel with the aid of geometrical instruments.
He then built up the painted surface in tempera and oil, recording the tiniest detail, down to each stitch or fastening of costume.
In the view of art historian Paul Ganz, "The deep glaze and the enamel-like lustre of the colouring were achieved by means of the metallic, highly polished crayon groundwork, which admitted of few corrections and, like the preliminary sketch, remained visible through the thin layer of colour".

The result is a brilliant portrait style in which the sitters appear, in Foister's words, as "recognisably individual and even contemporary-seeming" people, dressed in minutely rendered clothing that provides an unsurpassed source for the history of Tudor costume.
Holbein's humanist clients valued individuality highly.
According to Strong, his portrait subjects underwent "a new experience, one which was a profound visual expression of humanist ideals".

Commentators differ in their response to Holbein's precision and objectivity as a portraitist.
What some see as an expression of spiritual depth in his sitters, others have called mournful, aloof, or even vacant.
 "Perhaps an underlying coolness suffuses their countenances," wrote Holbein's 19th-century biographer Alfred Woltmann, "but behind this outward placidness lies hidden a breadth and depth of inner life".
Some critics see the iconic and pared-down style of Holbein's later portraits as a regression.
Kenyon Cox, for example, believes that his methods grew more primitive, reducing painting "almost to the condition of medieval illumination".
Erna Auerbach relates the "decorative formal flatness" of Holbein's late art to the style of illuminated documents, citing the group portrait of Henry VIII and the Barber Surgeons' Company.
Other analysts detect no loss of powers in Holbein's last phase.

Until the later 1530s, Holbein often placed his sitters in a three-dimensional setting.
At times, he included classical and biblical references and inscriptions, as well as drapery, architecture, and symbolic props.
Such portraits allowed Holbein to demonstrate his virtuosity and powers of allusion and metaphor, as well as to hint at the private world of his subjects.
His 1532 portrait of Sir Brian Tuke, for example, alludes to the sitter's poor health, comparing his sufferings to those of Job.
The depiction of the Five wounds of Christ and the inscription "INRI" on Tuke's crucifix are, according to scholars Bätschmann and Griener, "intended to protect its owner against il
For Holbein, "everything began with a drawing". A gifted draughtsman, he was heir to a German tradition of line drawing and precise preparatory design. Holbein's chalk and ink portraits demonstrate his mastery of outline. He always made preparatory portraits of his sitters, though many drawings survive for which no painted version is known, suggesting that some were drawn for their own sake. Holbein produced relatively few portraits during his years in Basel. Among these were his 1516 studies of Jakob and Dorothea Meyer, sketched, like many of his father's portrait drawings, in silverpoint and chalk.
Holbein painted most of his portraits during his two periods in England. In the first, between 1526 and 1528, he used the technique of Jean Clouet for his preliminary studies, combining black and coloured chalks on unprimed paper. In the second, from 1532 to his death, he drew on smaller sheets of pink-primed paper, adding pen and brushwork in ink to the chalk. Judging by the three-hour sitting given to him by Christina of Denmark, Holbein could produce such portrait studies quickly. Some scholars believe that he used a mechanical device to help him trace the contours of his subjects' faces. Holbein paid less attention to facial tones in his later drawings, making fewer and more emphatic strokes, but they are never formulaic. His grasp of spatial relationships ensures that each portrait, however sparely drawn, conveys the sitter's presence.
Holbein's painted portraits were closely founded on drawing. Holbein transferred each drawn portrait study to the panel with the aid of geometrical instruments. He then built up the painted surface in tempera and oil, recording the tiniest detail, down to each stitch or fastening of costume. In the view of art historian Paul Ganz, "The deep glaze and the enamel-like lustre of the colouring were achieved by means of the metallic, highly polished crayon groundwork, which admitted of few corrections and, like the preliminary sketch, remained visible through the thin layer of colour".
The result is a brilliant portrait style in which the sitters appear, in Foister's words, as "recognisably individual and even contemporary-seeming" people, dressed in minutely rendered clothing that provides an unsurpassed source for the history of Tudor costume. Holbein's humanist clients valued individuality highly. According to Strong, his portrait subjects underwent "a new experience, one which was a profound visual expression of humanist ideals".
Commentators differ in their response to Holbein's precision and objectivity as a portraitist. What some see as an expression of spiritual depth in his sitters, others have called mournful, aloof, or even vacant.  "Perhaps an underlying coolness suffuses their countenances," wrote Holbein's 19th-century biographer Alfred Woltmann, "but behind this outward placidness lies hidden a breadth and depth of inner life". Some critics see the iconic and pared-down style of Holbein's later portraits as a regression. Kenyon Cox, for example, believes that his methods grew more primitive, reducing painting "almost to the condition of medieval illumination". Erna Auerbach relates the "decorative formal flatness" of Holbein's late art to the style of illuminated documents, citing the group portrait of Henry VIII and the Barber Surgeons' Company. Other analysts detect no loss of powers in Holbein's last phase.
Until the later 1530s, Holbein often placed his sitters in a three-dimensional setting. At times, he included classical and biblical references and inscriptions, as well as drapery, architecture, and symbolic props. Such portraits allowed Holbein to demonstrate his virtuosity and powers of allusion and metaphor, as well as to hint at the private world of his subjects. His 1532 portrait of Sir Brian Tuke, for example, alludes to the sitter's poor health, comparing his sufferings to those of Job. The depiction of the Five wounds of Christ and the inscription "INRI" on Tuke's crucifix are, according to scholars Bätschmann and Griener, "intended to protect its owner against il
Hans Holbein the Younger