They were close friends by 1504, when Castiglione made his second visit to Urbino, as Raphael was gaining recognition as an artist in the humanist circle of the city's ducal court.

Castiglione is seated against an earth-toned background and wears a dark doublet with a trim of squirrel fur and black ribbon; on his head is a turban topped by a notched beret.

[4] The lightest areas are the subject's face seen nearly head-on, a billow of white shirt front at his chest, and his folded hands, which are mostly cropped at the bottom edge of the canvas.

[7] Art historian Lawrence Gowing noted the counter-intuitive handling of gray velvet (actually a fur) as contrary to an academic modeling of form, with the broad surfaces banked in rich darkness and the fabric shining most brightly as it turns away from the light.

[4] Yet the Castiglione portrait transcends questions of influence; art historian James Beck wrote that "The Portrait of Baldassare Castiglione stands as a final solution for single male portraiture within the Renaissance style...."[8] Notwithstanding shifts in the critical appraisal of Raphael's work, the painting has enjoyed consistent admiration from other artists.

is generally seen as owing a strong compositional debt to Raphael's painting, and also reflects Castiglione's influential advice regarding the restrained elegance of attire recommended for courtiers.

[12] At the turn of the 20th century Henri Matisse copied the painting, and Paul Cézanne exclaimed of Raphael's portrait: "How well rounded the forehead is, with all the distinct planes.