The article investigates the employment conditions of young early school leavers in Italy in the aftermath of the economic crisis, a period which was marked by a process of occupational downgrading. The empirical analyses rely on the 2005 and 2014 waves of the ISFOL-PLUS survey and show that the employment opportunities of youth who dropped out of school have substantially deteriorated over time, both in absolute terms and compared to those who attained an upper-secondary level certificate. The article discusses possible determinants of this negative trend. On the one hand, the increased negative selection of the group of early school leavers. On the other hand, the process of “crowding out” of workers with intermediate qualification levels from well-matching jobs. The results also show considerable gender differences and in particular the existence of a multiplicative disadvantage for female early school leavers, especially in Southern Italy.