Various studies suggest that rather than being a general trend that concern all individuals and all life domains uniformly, the de-standardization of the life course has taken distinct shapes and has followed distinct paces in various countries and social groups. In that respect, the gender divide may play a key role in de-standardization processes. The paper empirically tests cohort and sex effects on quantified indexes of de-standardization based on data from the Swiss Household Panel. Optimal matching is used in order to uncover whether these trends and their gendering, if any, may be accounted for by the development of new types of trajectories. A strong impact of cohorts on indices of de-standardization was found for both family and occupational trajectories. Gender effects mainly concern occupational trajectories. The results are discussed in light of the master status hypothesis.