Among the finest of Agostino's drawings, this work is also an outstanding example of Bolognese naturalistic portraiture of the late sixteenth century. Probably dating from the 1590s, during the artist's stay in Rome, the drawing bears a striking resemblance to Agostino's painting of Anna Parolini Guicciardini (Gemäldegalerie, Berlin), which is signed and dated 1598. The Museum's drawing, however, communicates the identity of the sitter with more unsparing veracity and greater psychological immediacy than is found in any of Agostino's late painted portraits of women. Much of its expressive force derives from the woman's intent gaze. Agostino subtly distinguished between her seeing and her blind eye, not only by contrasting the anatomical details but also by changing his handling of the red chalk medium—the tonal scale, the line weight, and the direction of the hatching.

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