The aim of this research was to study (a) trends in culturally sensitive factors (gender equity, collaboration, deference, competition, modeling, and congruence), of students in lower secondary (LS), upper secondary (US), and tertiary (TS) learning environments and (b) the gender differences in these trends. The study included 2,212 subjects (LS, 41.2%; US, 37.2%; TS, 21.5%; male, 39.3%; female, 60.7%) from Brunei. Data were collected by administering the Classroom Learning Environment Questionnaire (CLEQ) to the students. A steady increase in gender equity was observed from LS, through US to TS. The mean values on deference, modeling, and congruence scales were comparable for LS and US, whereas values decreased significantly for TS. It is also important to find ways to improve the magnitude of the factors in those educational institutions where students perceived low values.