This study explores the ways in which a group of preschool children enacted gendered social and occupational roles in their imaginary play. The research question interrogates the ways children reproduce or produce new meanings about the social and occupational roles of being boys and girls during unstructured play in the play-house corner in a preschool classroom. Data were collected through fieldnotes, photographs, and audio records and transcriptions of children's play narratives over a period of five months in a preschool setting in Riyadh, Saudi Arabia. The analyses discussed in this paper focus on three selected play episodes in which five preschool children constructed and negotiated their understanding of various social and occupational roles in their everyday experiences. The selected play narratives portray children's awareness of the acceptable and recognizable gendered practices in their cultural world. Children's understanding of the interdependence between gender and social and occupational roles is present across their storylines and performance. The children recognized the social positioning of gender. They also challenged existing gender norms through subtle ways, particularly disguise.