Educational leadership styles play a pivotal role in enhancing learning quality, improving school effectiveness, and elevating the performance of teachers and students. This study aims to conduct a comparative analysis of educational leadership styles in schools across Iran, Japan, Finland, South Africa, and Australia. These countries were selected based on the framework of "social systems with divergent educational outcomes." The research employed a documentary data collection method and utilized Bereday’s comparative approach for analysis. Findings reveal that distributed, participatory, and learning-oriented leadership styles dominate in Finland and Australia, closely tied to their decentralized structures, institutional trust, and emphasis on teachers’ professional development. In contrast, authoritarian and hierarchical leadership styles prevail in Iran and Japan, largely rooted in organizational culture and centralized educational systems, though Japan exhibits emerging tendencies toward participatory leadership due to its collectivist cultural norms. South Africa, shaped by its unique historical context, employs a hybrid of transformational, situational, and context-aware leadership styles. The study identifies educational system structures, organizational culture, economic conditions, and leadership selection processes as critical determinants of leadership styles. The research recommends that policymakers in centralized systems prioritize school autonomy reforms, revisions in managerial appointment mechanisms, and strengthened professional development programs to foster higher-quality educational leadership.