The aim of this research was to examine predictive factors of entrepreneurial orientation of students in transitional, social, and economic contexts. Attitudes towards work, value orientations, gender, and the entrepreneurial experience of the father and the mother of the respondents were examined as predictor variables. The sample comprised 220 students from both genders with an average age of 21.57 years. The results indicate that, in all three measured components, young men have a more pronounced entrepreneurial orientation compared to young women. Attitudes towards work and organizational values were shown to correlate significantly with entrepreneurial orientation. Experiencing work as an opportunity for personal fulfilment (β = 0.420, sig <0.001), autocratic value orientations (β = 0.269, sig <0.05), and the entrepreneurship of the father were distinguished as significant predictors of entrepreneurial orientation on the total sample (β = 0.211, sig <0.001), as well as on the subsample of young women (β = 0.283, sig <0.05). The results of this research indicate the complexity of relationships between the examined factors and entrepreneurial orientation, the conversance of which provides the basis for conceptualizing the entrepreneurial socialization of young people in a particular social and economic context.