This chapter explores the intersecting influences of national gender regimes and occupational structures on gender inequalities. Focusing on the legal profession as a case study and using a comparative mixed-method design of Swiss and French lawyers at an early career stage, the chapter highlights how national gender regimes and occupational structures interact and shape gendered career paths and gender inequalities in unexpected ways. In particular it shows that Swiss women lawyers’ chances to climb up the occupational ladder are significantly higher than their French women counterparts, despite a less favourable gender regime and a greater ‘motherhood penalty’ for Swiss female professionals. The chapter also shows how the structural changes currently sweeping across legal labour markets contribute to a widening gap between different generations of lawyers in a particularly stark way in the French case. The conclusion underlines the insights gained from a cross-national comparative study paying attention to the interactions of the gender order and of the occupational structures of different labour markets. Such an approach sheds a heuristic light on the various and conflicting trends at play in the dynamics of inequalities.