The impact of the family environment, the mode and the quality of parental stimulation may have a decisive role in the student’s capacity development and realization of given capabilities, and affects particularly the level and the quality of his/her academic attainment. A student’s academic attainment is conditioned by educational aspirations formed in a dynamic interaction with stimulating aspects of the family context. The aims of our study were: to examine the students’ attitudes towards schooling, and to obtain answers to the question: which stimulating aspects of family context are the most predictable for the development of educational aspirations, i.e. attitudes towards school and gaining knowledge, educational interests and plans for further education. The sample comprised 1.464 eighth-grade students, aged 15, from 34 primary schools in Serbia. The data were collected by the use of questionnaires filled in by the students and school principals. The results indicate a trend of interrelatedness of cognitively and educationally favorable conditions within the family and positive attitudes towards school, attainment, high aspirations and cognitive and intellectual interests for out-of-school activities. It can be concluded that family stimulation is the resultant of the influence of cultural and educational profile of the family and active parental attitudes regarding education and attainment of their children. The findings could have practical implications in the domain of parents/school cooperation, not only in order to increase the awareness of the importance of active participation of both parties, but also to provide useful guidelines for developing optimal contents and procedures. .