Since the 1970s, her works have addressed topics such as identity, gender and social roles, examining stereotypical media representations of women. By adopting a multitude of disguises and personae, the artist invites the viewer to take a critical stance on subjectivity and sexuality.

The performative stance of each character is emphasized by their extravagant outfits, resulting in an almost stage-like, theatrical impression. Untitled #614, for example, depicts a man posing confidently before a tree-lined avenue. His posture and attire—silk trousers with flowers and an embroidered cape—radiates both confidence and femininity, thus challenging stereotypical contemporary perceptions of gender.

For the couple featured in Untitled #609, the artist used the same wig and makeup for each character, through to their facial hair. Gender here is thus only attributable superficially based on the figures’ conventional accessories: hat, earrings and purse.

Since her earliest works, Sherman has played with masculinity and gender expression. In Bus Riders and Murder Mystery, two series from 1976, she impersonates both men and women of different age, color and social status, using elaborate disguises to hide her individuality behind stereotypical character representations. In the diptych Doctor and Nurse (1980–87), Sherman stages herself in a clichéd depiction of a 1950s male doctor and female nurse; and her mise-en-scène as clergymen and aristocrats in History Portraits (1988–90) comments critically on the male-dominated nature of European art history. Finally, the notion of gender is eliminated entirely in her more recent Clown series (2004) by means of thick layers of face paint and shapeless costumes.