A consolidated sociological line of the research allows us to understand the educational advantages of middle-class pupils in terms of the dynamics of reproduction [Bourdieu, P., and J. C. Passeron. 1970. "The Inheritors: French Students and Their Relations to Culture," translated and edited by Richard Nice. Chicago: University of Chicago Press; Power, S., T. Edwards, G. Whitty, and V. Wigfall. 2003. "Education and the Middle Class." Buckingham: Open University Press]. However, some scholars have pointed out how this process cannot be taken for granted, highlighting the difficulties experienced by youths in reaching academic success [Reay, D., and H. Lucey. 2002. "Carrying the Beacon of Excellence: Social Class Differentiation and Anxiety at a Time of Transition." "Journal of Education Policy" 17 (3): 321-336. Doi:10.1080/02680930210127586]. Based on Bourdieu's perspective, this article will explore the links between low educational attainment, artistic passion, and high aspirations in privileged students. The research is based on in-depth interviews and focus groups with middle-class pupils in two secondary art schools in Milan. It is argued the artistic disposition acts within dynamics of negotiation among different and contrasting expectations. Creativity emerges as a source to perform gendered privileged learner identities. This study on artistic educational pathways can contribute to understanding the process-making of inequalities in creative fields.