The aim of this article is to acquire knowledge regarding children’s influence and the construction of gender during free play situations in preschools in different local contexts. Attention is focused on both children’s choices and pedagogical practices in which free play takes place. The research draws on ethnographic studies based on participant observation and group interviews of teachers and children in different contexts (high-income, immigrant, rural). Following deep immersion in the data, interpreted through the lens of Basil Bernstein’s conceptualisation of power and control, in combination with gender theories, the research finds that play choices are strongly affected by norms and by what is “on offer” in the different preschool contexts. The analysis shows two dominant patterns of play that are salient; gender-stereotyped choices primarily divided into “girl and boy groups”, and mixed choices with no clear gender-based division. The article argues that free play provides good opportunities to resolve the tensions between gender equality and steering of teachers, especially when clear pedagogical ideas guide the play offer in preschools. In such cases, gender equality and teacher influence can work in synergy in order to allow children’s influence on free play to emerge without contradicting gender equality ideas.