Feminist legal scholars have repeatedly highlighted the necessity of understanding gender stereotyping as one limit to women’s emancipation. Anti-stereotyping, developed as a political ideal by EU legislators, aims to free each and every individual from traditional gendered norms. It has however long been confined to the arena of soft law, making only recently a timid entry in the preambles first of the Work/Life Balance Directive, and then of the Women in Boards Directive. Faced with this legislative silence, the CJEU has developed since the 1980s its own meaning of anti-stereotyping, parallel to the persistence of its cases actively stereotyping women. As a result, the Court developed, simultaneously with the use of gender stereotyping in other judgments, anti-stereotyping arguments. Nevertheless, the role of anti-stereotyping in achieving real equality and women’s emancipation needs to be questioned. By assessing the genealogy and the scope of the anti-stereotyping approach in EU gender equality jurisprudence, this thesis reveals the mixed results of anti-stereotyping reasonings for women, from a substantive perspective which understands inequality as a structural and systemic phenomenon. First, the development of anti-stereotyping is shown to be a gendered process, from the perspectives both of its use by mainly men applicants, and of its reception by the Court. In practice, anti-stereotyping reasoning is more often used to guarantee men rights to embrace non-traditionally masculine activities, than to ensure women’s rights to perform traditionally masculine ones. Second, the European anti-stereotyping approach rests upon the assumption that freeing individuals from pre-conceptions on their abilities will enable them to choose their own path, ignoring the social constraints and the structural discriminations faced by women. Ultimately, in its understanding and use of anti-stereotyping, the Court has failed to grasp its full transformative potential, and its jurisprudence in turn serves an androcentric, liberal and individualist understanding of gender equality.