In comparison with curriculum studies, teaching?learning methods or art program development, evaluation is one of the areas that have been left unexamined in the art educational field. The emphasis on sensitivity, originality, diversity and creativity often leads us to regard evaluation as hinderance. Not only does this attitude prevent us from being equipped with fully developed evaluation systems and methods, but also it puts us in lack of the appropriate language needed to develop the full range of discourse on evaluation. Therefore, this study investigates the controversial issue of evaluation in art education from the social and cultural perspective. It purports to generate the conceptual framework that helps us to communicate about this current issue from multi-faceted approaches and to initiate the discourse on the alternatives of evaluation in education. In this respect, the concept of ‘habitus’ by Pierr Bourdieur is used to explain the process of acculturation through schooling and evaluation. In addition, four features of curriculum -explicit curriculum, implicit curriculum, null curriculum, and curriculum shadow- are examined in a way of locating art in the context of schooling. Based on this cultural understanding of schooling, this study discusses the dilemma of evaluation in art education and the characteristics of art as a school subject. Finally this study argues that the contextual perspective and critical self-reflection are significant in order to search the alternatives of evaluation that would transform the distorted culture of schooling in our society.