Background: Whilst much interest is focused on gender, and classroom-level influences such as and classroom composition and teaching style on achievement, attitudinal outcomes have not received the same attention. This paper focuses on alienation from learning as one sub-dimension of school alienation. School alienation is a relevant issue for all those engaged in supporting students to thrive and have positive outcomes, as it is related to learning and social behaviour, and eventually achievement. Purpose: This explorative study considered how classroom gender composition and perceived teaching style affected the development of alienation from learning in primary and secondary schools. Methods: A multi-level analysis, based on quantitative longitudinal data gathered in Luxembourg, was undertaken. The database included information gathered during three consecutive waves (2016-2018) from 338 primary school students and 376 secondary school students. Findings: Our results indicate that the gender gap in alienation from learning was more pronounced in primary school. A student-centred supportive teaching style (classroom level) decreased alienation from learning in primary school for boys -- closing the gender gap; that is to say, it did change the difference in alienation between girls and boys. In secondary school, only individual-level perceived teaching style was associated with alienation if teaching style was simultaneously considered on both individual and classroom level. A high proportion of male students in the classroom seemed to go along with a higher alienation among all students in secondary school. Conclusion: This exploratory study indicates that teaching style may be a crucial factor for the attitudes towards school of all students, suggesting that employing student-centred and supportive styles could help to prevent school alienation.