Moving from the concepts of territory as a social construct and of development as the progressive, dynamic fulfilment of self-established goals, this paper aims to show how a genuine strategy of development helps build up sustainable attractiveness. To achieve this goal, it first investigates the accuracy of the Nation Brands Index as a signal of (positive or negative) territorial attractiveness, from a long-term perspective. Second, the pertinence of the freedom approach to development, in order to fully integrate the sustainability issues, is described. Finally, the two models are compared, thus allowing the mutual links and synergies to appear and corroborating the idea that appropriate development strategies lead to the emergence of a selective attractiveness, based on the territorial values and choices.