The aim of this article is to look critically at the implications of gender equality concepts for individual freedom as conceptualised by the philosopher Isaiah Berlin. The scientific literature addressing the problem of freedom and gender equality with regard to public policy is considerably fragmented. Based on contextual literature, this article will offer four concepts of freedom that serve as analytical categories. I will analyse work/family reconciliation policy tools as introduced at the level of the European Union and reconnect them to three traditions of gender equality. The article reflects on historically embedded dichotomy between positive and negative freedom visible in gendered distinction between public and private. The main findings show that the relationship between freedom and equality is mediated by the selected policy tools suggesting that some policy tools expand freedom of all individuals while others indicate a possible limit for freedom.