Currently there is a great inclination to modify sport and well-being concept by changing the technology in wearable especially thanks to the huge development of technologies in the field of smart textiles. Textiles of today are materials with applications in almost all our activities. Fibres, yarns, fabric and other structures with added-value functionality have been developed for a range of applications textile materials and the textile has become an important platform for high-tech innovations. Smart Textile creates textile products that interact by combining smart materials and integrated computing power into textile applications. The introduction of smart materials and computing technology in textile structures offers an opportunity to develop textiles with a new type of behavior and functionality. Smart Textile and computing technology are introducing a shift in textile, from a passive to a dynamic behavior, from textiles with static functionalities to products that exhibit dynamic functionalities. This work will describe the results of an educational activity carried out inside the Sportswear Studio Lab of Master Degree in Fashion Study at School of Design of Politecnico di Milano. The students were asked to generate a new advanced concept for sport application exploiting the potentiality of smart textile and wearable technology. The projects developed by the students followed a design approach suggested by the author that requires the understanding of: (i) the what (the purpose of the concept); (ii) the how (the used technology); (iii) the where (the context in which the product is used) and finally (iv) the wearability issues connected to the role of technology in human body changing and perception.