In this paper we describe the design process of an interactive accessory to play anywhere and anytime while encouraging free-play and practice social skills. We explain the design process, the resulting conceptual design of FeetUp and the preliminary user’s evaluation. FeetUp is a playful accessory that takes advantage of children’s interest to jump, or perform body stunts. These activities generally include lifting both feet, and FeetUp gives audiovisual feedback whenever this happens to encourage free-play related with jump activities. Preliminary user’s experience shows how FeetUp, encourages freeplay.