We observe a relevant growth in teacher’s perception of reduction of their social prestige, even if it seems stable according to the occupational prestige scales. This discrepancy seems even odder considering that, in the meanwhile, a process of professionalization of teaching took place. How could we explain this conflicting evidence? We use two different data sources: the survey on the social evaluation of the occupations (sidesø5) and three surveys of Italian teachers (from 1990 to 2008). We try to explain the contradiction between perceived and attributed social prestige considering major changes occurred in Italy in the Italian labor market and educational system. We theorize a relevant role played by the changing employment opportunities offered to women over time. Our hypotheses are confirmed for the social desirability of teaching, namely higher among women, especially the older ones. On the contrary, we find no support for our explanatory hypotheses about the growing perception of lower social recognition by the teachers themselves.