This chapter aims firstly at examining the impact of gender stereotypes on choosing vocational education or profession. Secondly, the relevant policies of European Union and Greece, in particular, are presented and commented upon. For this purpose, relevant data have been collected from four related surveys conducted in the years 2008, 2010, 2014, and 2017, mainly in the high schools of Attica (Greece). The results from these four surveys only partially confirm the original hypothesis, namely that the gender stereotypes influence the decision-making process of choosing a field of vocational study or profession, but also indicate that there are significant correlations between specific occupations per gender identity and stereotypical perceptions. Finally, the harmonious coexistence of the sexes requires the development of self-knowledge and critical thinking. This can be achieved only by raising the awareness of teachers, who are called to improve the critical self-knowledge and social knowledge of individuals through the implementation of policies regarding school and local society.