Vocational education and training (VET) is the most common post-compulsory pathway in Switzerland. Providing ready-to-use occupation-specific skills, VET has repeatedly been credited to provide smooth transitions to employment. However, the strong horizontal gender segregation within the Swiss VET system is linked to lower pays and restricted career and educational opportunities for women. This article studies the consequences of this gender segregation by looking at the school-to-work (STW) trajectories of new Federal VET Diploma (FVETD) holders over the medium term. Using sequence and cluster analysis of data from the administrative LABB database, it examines the trajectories of the 2012 FVETD graduate’s cohort over seven years, highlighting a great diversity of pathways into further education, employment, or NEET status. This article further focuses on the gender disparities in these pathways and looks at the specific consequences of evading the gender norms by enrolling into gender-atypical VET occupations. Our findings reveal that women are less likely to pursue further education and face greater challenges if they come from male-dominated VET trainings. Finally, this study examines the diversity of SWT trajectories through individuals’ allocation to a VET occupation using multilevel models, providing new insights into medium-term outcomes based on the type of training followed,