This paper is an attempt to analyze the transformation of the Islamic headscarf from being a private question of piety to a public question of freedom of religious expression. It argues that such a transformation constitutes not only the foundations of the emergence of the headscarf issue but also what we call headscarf-skepticism. The long-lasting headscarf issue has reached a point of deadlock once again due to the reactions of the secular sections of society to the recent efforts of the government to lift the headscarf ban. Different uses and meanings of the Islamic headscarf have reached an increased complexity since the foundation of the republic. It is argued that this complexity is due first to the elements of the history of the Turkish Republic, second to the emergence of new state-society relations, and third to the accelerated developments in the conflict between Islamists and secularists.