Research shows that a lower proportion of women than men are in graduate level jobs, six months after leaving seven top UK universities. This paper presents new empirical evidence from a unique dataset on the significantly different attitudes and behaviours between Oxford men and women undergraduates that might explain why women are less likely to have secured a graduate level job than men. Lower self-assurance, firmer beliefs in gender stereotypes, strong prestige and gender-characterisation of occupations, and favouring sectors with informal and low-status entry, all contribute to a lower proportion of women securing graduate level jobs. Despite many advances in recent years narrowing the gap between men and women, there remain policy implications for curriculum delivery and co-curricular courses to increase women's self-assurance and assertiveness, and thereby enable them to aspire to and then secure a wider range of higher prestige occupations.