This article addresses the question of life course de-standardisation in Portugal, drawing on a trajectory-based holistic approach. The de-standardisation hypothesis presupposes that, over recent decades, occupational and family trajectories became gradually more variable. Our methodological strategy to test these hypotheses uses entropy measures and assesses how cohort and gender influence standardisation. We used these measures to determine the heterogeneity in co-residence and occupational trajectories between the ages of 7 and 35. In a second stage, we used regression models to estimate if cohort, gender, education and socioeconomic class associate with co-residence and occupational entropy. The paper draws on data from the 'Family Trajectories and Social Networks: The life course in an intergenerational perspective' research project (n=1500), which included questions on co-residence and work employment history of Portuguese individuals born in three different cohorts (1935-40; 1950-55; 1970-75). Findings show that standardisation and de-standardisation dynamics coexist, operating differently depending on the life domain and the stage of life. While early family trajectories are more standardised in younger cohorts, later stages are slightly more diverse, particularly among women. As far as occupational trajectories are concerned, formative years are much more standardised in the younger cohort, while adulthood is de-standardised in all cohorts. We discuss results in light of the life course regime and gendering hypotheses.