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This study investigates the social values and systemic factors influencing female participation in educational leadership in Trinidad and Tobago. Despite women constituting the majority of the teaching workforce, they remain significantly underrepresented in senior leadership roles within the education sector. The purpose of the study is to examine how gendered social values, institutional practices, and intersecting personal and contextual factors shape access to and progression within educational leadership. The study was guided by three research questions examining (1) social values influencing female leadership participation, (2) factors contributing to inequality and underrepresentation, and (3) strategies to promote greater gender equity in leadership. An explanatory sequential mixed-methods design was employed. The population consisted of educators working in government and government-assisted schools in Trinidad and Tobago. A purposive sampling technique was used to select a sample of 33 male and female educators across two school contexts. Data were collected using a semi-structured survey questionnaire administered online. The instrument included both closed-ended and open-ended items designed to capture leadership perceptions, experiences, and institutional conditions. Instrument validity and reliability were supported through expert review and pilot testing procedures to ensure clarity, contextual relevance, and consistency. Quantitative data were analyzed using descriptive statistics and inferential testing, including independent-samples t-tests, while qualitative responses were examined using inductive thematic analysis. This integrated analytical approach enabled identification of broad statistical patterns alongside deeper insight into participants’ lived experiences and interpretations. Findings indicate that while gender equity policies exist within the education system, their practical impact is limited by inconsistent implementation, persistent gender stereotypes, and structural constraints. Key barriers include culturally embedded caregiving expectations, gendered perceptions of leadership suitability, uneven access to mentorship and sponsorship, and organizational practices that privilege linear, uninterrupted career pathways. Results also show that leadership participation is shaped by the combined effects of social values, family responsibilities, organizational structures, and individual self-efficacy. The study concludes that gender-inclusive leadership frameworks can strengthen institutional effectiveness and decision-making in education. It recommends the adoption of gender-responsive leadership development programs, formalized mentorship and sponsorship structures, family-supportive workplace policies, and stronger accountability mechanisms to support equitable leadership pathways. By providing context-specific empirical evidence, the study contributes to Caribbean scholarship on gender and educational leadership and offers practical guidance for policymakers and educational stakeholders seeking to advance inclusive leadership systems.