In this article, we read and analyse selected young adult novels by Chinese-German author Wei Cheng that address the dilemmas faced by young female Chinese immigrants in Western countries. The aim is to explore the ways in which the construction of femininity and gender are inextricably bound up with categories of race and ethnicity in China-West encounters, and to probe the dynamics of such encounters embedded in the larger socio-political power structures. Through a critical analysis of the representation of Chinese femininity vis-à-vis Western masculinity, the essay interrogates the workings of the “Orientalist gaze” in relation to patriarchy and gender politics. The portrayals of the cross-racial encounter in Shaonv de Hong Chenyi (The Girl’s Red T-Shirt), which reiterate received ideas about the Orient, may be read as a product of self-Orientalisation, where the intriguing position of the adolescent Chinese girl prompts a rethinking of postcolonial gendered subjectivities. While self-Orientalisation may work to legitimate the discourse of Orientalism, the reading of Shaonv de Hong Faqia (The Girl’s Red Hairpin) reveals the ways in which self-Orientalisation could function as strategic essentialism that allows the female “Oriental” Other to gaze back and stand Orientalism on its head. The marriage between gendered and postcolonial approaches to children’s and young adult texts promises to act as a crucial intervention in the global struggle against hegemony.