Background and objectives: Psychosocial factors, such as gender role norms, may impact how social anxiety disorder (SAD) is experienced and expressed in different social contexts for women. However to date, these factors have not been examined via experimental methodology. Design: This was a cross-sectional, quasi-experimental controlled study. Methods: The current study included 48 highly socially anxious (HSA) women (70.9% meeting criteria for SAD) and examined the relationships among psychosocial factors (i.e. gender role self-discrepancies and self-perceived physical attractiveness), self-perceived social performance, and state anxiety, across two in vivo social tasks (i.e. conversation and opinion speech). Results: On average, participants reported belief that they ought to be less feminine for the speech task and more masculine for both the conversation and speech tasks. Also, for the conversation task, only lower self-rated attractiveness predicted poorer self-perceived performance and greater post-task state anxiety, above gender role self-discrepancies and confederate gender. For the speech task, only greater self-discrepancy in prototypical masculine traits predicted poorer performance ratings, and it was related to greater state anxiety in anticipation of the task. Conclusion: For HSA women, psychosocial factors may play different roles in social anxiety across social contexts.