Objective: This study investigates how multiple domains of parental gender role socialisation as well as parent-child relationships and family structure may shape adolescents’ gendered occupational aspirations. Background: Young people with gender-typical aspirations have a higher chance of choosing gender-typical post-secondary education fields and are more likely to work in gender-typical occupations as adults. Gender norms, family structures and parent-child relationships have undergone profound changes in recent decades. We extend the intergenerational transmission literature by considering whether the influence of parental role modelling may vary according to parent-child relationships and family structure. Method: We draw on data from 2,235 adolescents from the German Socio-Economic Panel and apply logistic regressions. Results: Children whose fathers were employed in gender-typical jobs had a greater likelihood of aspiring to a more gender-typical occupation. This relationship was not significant among sons who did not live continuously with both parents since birth, who were generally more likely to aspire to gender-typical occupations. Surprisingly, the gender-typicality of fathers' occupations seemed more influential among daughters whose parents had separated than among those who lived continuously with both parents. Regarding the parental gender division of paid and unpaid work, only mothers' continuous non-employment was associated with daughters being more likely to aspire to a gender-typical occupation. Conclusion: On the whole, our findings suggest a rather weak influence of parental gender role modelling on children’s persistently gendered occupational aspirations in Germany. Yet, our study extends existing family research by pointing to significant variations across family structures.