Anonymous Art – Crossdressing

ByKaren Posted on Updated on Art Gallery

Cross-dressing is the act of wearing items of clothing not commonly associated with one's sex. Cross-dressing has been used for purposes of disguise, comfort, and self-expression in modern times and throughout history. Almost every human society throughout history has had expected norms for each gender relating to style, color, or type of clothing they are expected to wear, and likewise most societies have had a set of guidelines, views or even laws defining what type of clothing is appropriate for each gender.

The term cross-dressing refers to an action or a behavior, without attributing or implying any specific causes or motives for that behavior. Cross-dressing is not synonymous with being transgender.
Feminization, sometimes forced feminization and also known as sissification, is a practice in dominance and submission or kink subcultures, involving reversal of gender roles and making a submissive partner take on a feminine role, which may include cross-dressing.

For the cross-dressing artworks in the albums below I was unable to determine the artist. To view more crossdressing art use the tag Crossdressing.

3 albums/51 artworks
Lastest Update: January 18, 2026 -> Updated 1930 Crossdressing (16 artworks)

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