Contributions of John Dewey`s aesthetic theories have long been recognized by artists and designers. The aim of this paper is to discuss how some ideas held by the influential American philosopher may aid in conceiving and carrying through a design educational program. One of the most often raised questions in design education is the role of art-based concepts versus strategic business approaches. If we are to take Dewey`s arguments on account, it should be clear that extreme positions would be undesirable, as almost every aspect of his philosophical thoughts tend to reject dichotomies, judging them as false oppositions that are mistakenly taken as natural. This seems to be especially helpful in the case of design, which emerges during the twentieth century as a complex and interdisciplinary field. While Dmitri Siegel characterizes design as the “sliver of land suspended between culture and commerce”, Dewey`s aesthetic comments could lead us to seeing a continuity between these territories. In this sense, design would be immersed in the encountered waters of culture and commerce, rather than suspended over it. It becomes impossible then to sustain a design education program that focus either on “liberal arts” or “mechanical arts”. This classical division leads to an unwanted hierarchization of human activities, which ignores the fact that what constitutes usefulness in Dewey`s pragmatic view is “contributing directly and liberally to an expanding and enriched life”. It becomes necessary to overcome this dichotomy, if one expects to offer an educational program that can give weight and relevance to the skills that are intrinsic to the activities of a designer in a creative economy.