Various studies have shown how institutional arrangements in education determine further education and occupational opportunities. By combining the wider literature on the effects of institutional arrangements with the studies on pupils’ aspirations, this chapter aims to explore how institutional arrangements in education may influence pupils’ aspirations. For this, we contrast the stories of two 15-year-old ethnic white working-class girls with a similar aspiration, but attending two internationally very different schools, namely a Dutch lower vocational secondary school, and an English state-funded comprehensive secondary school. Their stories were recorded over a two-year period as part of a larger ethnographic study on the aspiration of ethnic white working-class girls in secondary schools. Through the concepts, reasons and resources of pupils’ aspirations these stories will be analysed to unravel how specific features in the Dutch and English education systems influence the distinctive ways of shaping their aspirations.