Over the last decades, female educational attainment has progressively caught up with male one in many OECD countries. Expectations of university graduation have correspondingly been found to be higher among female adolescents than among male ones. The advantage is even higher for girls of lower social origin. In the present research, multilevel modelling is applied to a combination of national-level data, on the one hand, and individual- and school-level data drawn from PISA 2003 on the other hand, in order to explain lower expectations of university graduation among male kids of lowly educated parents. Attention is paid to gender egalitarianism, educational differentiation and economic structure. A more gender-egalitarian society is expected to make human capital investment more attractive for girls. This effect may not affect expectations of university graduation among offspring of highly educated fathers, but it is expected to raise educational expectations of daughters of lowly educated fathers well above expectations of boys of the same origin. As regards educational differentiation, vocational training may become more appealing for male kids of lower social origin than for female ones. Finally, the size and growth of employment and wages in strongly masculinised sectors (i.e. manufacturing and construction) may divert male kids from entry into university, making vocational training or straight entry into the labour market more attractive. Again, this effect could be stronger among male adolescents of lower social origin. The evidence supports the role of the economic structure and gender egalitarianism, but no evidence is found in support of the role of educational differentiation.