This research study aims to investigate the significance of the gender of secondary school head teachers in influencing their leadership styles within the context of Pakistan. Pakistan’s cultural milieu is characterized by patriarchal undertones that translate into low gender equality, particularly in terms of lower educational attainment and lesser professional opportunities for females as compared to males. Within this setting, this thesis views the relationship between gender and educational leadership through the feminist educational leadership perspective, while the contextual environment is analysed by employing an adaptation of Brofenbrenner’s ecological development theory. A mixed-methods research design has been used to answer this study’s research questions. The quantitative research method is based on a survey that was administered to a random sample of 350 secondary school head teachers belonging to the public and private sectors within nine districts of the Punjab province in Pakistan. The self-rater Multifactor Leadership Questionnaire was used to determine the self-perceptions of head teachers regarding their leadership styles. In addition, the qualitative research method utilizes semi-structured interviews of a purposive sample of 14 head teachers in order to obtain an in-depth understanding of how the contextual environment is perceived by head teachers and to investigate whether the head teacher’s gender is a significant factor in influencing these perceptions within Pakistan’s context. The survey generated 264 responses and the findings indicate that on average secondary school head teachers perceive their leadership style as being transformational; particularly private sector female head teachers have the highest mean score for the transformational leadership style, hence suggesting that the gender of secondary school head teachers does play an important role in terms of influencing how they assess their leadership styles in Pakistan’s context. Furthermore, the qualitative analysis of the interviews reveals important gender-based differences in terms of how head teachers perceive their contextual environment and how they practice transformational leadership within their schools. This study’s findings have implications for theory, practice and policy making in the field of educational leadership, as they emphasize the need for implementing gender-sensitive educational policies that may facilitate both male and female head teachers to perform their roles effectively as school leaders within Pakistan’s context.