This qualitative study examines how critical reflexivity is manifested in and enacted by seven Social Studies teachers, in the Singaporean context of ethnic diversity, increased affluence and socio-political constraints. The cases show that critically reflexive teachers are strongly influenced by their lived experiences to develop good self-understanding and a deep sensitivity to systemic inequalities around them. Critical reflexivity presents as a continuum, with most teachers working towards improving their students’ critical thinking and awareness to inequity through their teaching, while some undertake personally transformative journeys that also effect change in their immediate communities. Findings provide insights on the motivations behind critically reflexive attitudes, and also point to factors that hinder a greater development of critical reflexivity. We suggest that critical reflexivity attitudes can be developed in teachers via programs such as currere, for enhanced teaching practice. Findings also highlight the nuances in the nature of citizenship values in the Asian context, suggesting that critical reflexivity involves small and subtle actions of change and agency in teacher-practitioners.