This article assesses the employment and occupational outcomes of upper secondary education graduates from academic and vocational tracks in Italy. In particular, we formulate and test the hypothesis that – contrary to some common expectations – academic graduates outperform vocational graduates at a stage of occupational maturity, even when considering individuals without a tertiary degree. Moreover, we explore differences between tracks by gender as well as across geographical areas and city sizes. Thanks to the detailed information available in the PLUS data, we assess labor market outcomes adjusting for a rich set of socio-demographic characteristics and for early academic performance. The results corroborate our hypothesis and indicate that the advantage of academic graduates holds across genders, areas and different city sizes.