Using the Labour Force Survey 2013, this paper examines gender differences in holding supervisory positions in 26 European countries and relates these differences to horizontal gender segregation, i.e. women and men working in different jobs. First, we confirm the findings of previous studies that women are still disadvantaged in holding supervisory positions in almost all countries. Second, by examining how women’s disadvantage varies when working in male-dominated, gender-mixed, and female-dominated occupations, we observe women’s lowest disadvantage in male-dominated occupations in most countries. Third, applying a two-stage multilevel analysis, we explore at the macro level how the country variation in women’s disadvantage in holding supervisory positions is related to horizontal gender segregation, selection of women in the labour market, and conditions facilitating the combination of work and family, and whether women’s disadvantage significantly differs among welfare regimes. We provide evidence that differences among welfare regimes capture much better country variation than single macro indicators.