The aim of this thesis is to analyze gender differences across contemporary societies, with the following main research questions: First, do gender differences exist among labor market entrants and the whole labor market population? And does the extent of gender differences vary from country to country? Second, can conventional country groupings and countryspecific characteristics – family policies, the gender culture, and labor market related setups – contribute to the explanation of this country variation? To answer my research questions, I rely on comparative cross-sectional data from the Labour Force Survey (LFS) from 2009 and 2013 and the Programme for the International Assessment of Adult Competencies (PIAAC) from 2011/12. The main empirical analysis strategy is twostep multilevel models. I distinguish between a horizontal and a vertical dimension of gender differences in the labor market and examine several different indicators to offer a comprehensive picture of gender differences. At labor market entry, horizontal gender differences seem to be already pronounced in all countries, while my findings indicate that females are not yet disadvantaged in vertical gender inequalities (in terms of entering high-status occupations) in several countries. In turn, for the whole labor market population, I find a female disadvantage in working in supervisory positions and participating in employer-financed training in nearly all countries. Countries vary notably in the extent of their gender differences, indicating that countryspecific setups play a role. For horizontal gender differences at labor market entry, however, I can not identify a strong association with any of the theoretically important macro factors I examined: Neither the gender culture nor the share of women in public sector employment contributes notably to explaining country variation. In contrast, females seem to have better chances of entering high-status occupations and participating in employer-sponsored training in countries with family policies supporting females' full-time and continuous employment (i.e., shorter parental leave and higher childcare provision). I further identify a more traditional gender culture to be detrimental to women's chances of participating in employersponsored training. Finally, females disadvantage in entering high-status and supervisory positions is higher in countries with higher female employment.