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Previous research has shown that there are distinct types of children’s shyness within eastern and western cultures, with different origins, developmental courses, and outcomes. A major limitation of this prior work, however, has been that measures used to examine children’s shyness in eastern contexts have been developed almost exclusively in the North American context. Whether shyness subtypes and their predictive associations are conserved between western and eastern cultures on a children’s shyness measure developed in an eastern context is an empirical question. Here we examined 1) whether two Chinese shyness subtypes, (i.e., regulated and anxious), as defined by the implicit perspective of Chinese children, also occurred in a western context, and 2) if so, whether the two types of shyness were equivalent (i.e., invariant) between cultures and also differentially associated with social anxiety based on culture. The participants were children aged 3-5 years from China (n = 182, 53.8% boys) and Canada (n = 201, 42.3% boys), the latter group completing a translated version of the parent-reported Chinese Shyness Scale (CSS, Xu et al., 2007). The findings indicated that the two shyness subtypes and the one-factor social anxiety construct existed in both cultures and that the CSS and the social anxiety construct were also equivalent across the country. Subsequently, latent moderation structural equation modeling revealed significant interaction effects of regulated and anxious shyness subtypes by country on social anxiety, respectively. Furthermore, the two distinct shyness subfactors interacted differentially with social anxiety based on the cultural group. Regulated shyness was significantly and positively related to social anxiety in Canadian children, but not in Chinese children. Conversely, anxious shyness was significantly and positively related to social anxiety in children from both countries, but more strongly in Canada. Findings are discussed regarding possible cultural explanations for why the relations between two types of shyness and social anxiety are different in western and eastern contexts and their implications for understanding cross-cultural differences in personality development.