This article considers how the complexity and the destandardization of early-careers have changed across cohorts in Italy. The evolution of both indicators is connected with the perspective of stabilization in the labour market for the cohorts entered in activity before, during, and after the introduction of the deregulation reforms. We use longitudinal data from social security archives (INPS) on employment episodes matched with the Italian EU-SILC 2005 sample on the first seven year of participation. By applying sequence analysis techniques, we identify remarkable differences in early-career complexity across cohorts of women, to the disadvantage of low-educated women. Destandardization concerned especially women in general, and highly-educated in particular.