This essay provides a comprehensive interpretative framework to understand the reasons why the school-to-work transition is so slow in Italy, a typical example of the South European regime, where the educational system is rigid and sequential (education before work experience), the labor market has become more flexible through two-tier labor reforms and the family has an important role of shock absorber during the passage to adulthood. The main thesis of this essay is that the traditional disorganization of the educational and training system coupled with slow economic growth, rather than only low labor flexibility explains high (youth) unemployment. Important reforms -- Jobs Act, Good School, European Youth Guarantee and reform of employment services -- have been recently implemented, which are favoring a slow convergence toward the European social model, but it is still too early to draw conclusions as to the impact of such reforms on youth labor-market outcomes.