PEGASO is a FP7-funded project whose goal is to develop an ICT and mobile-based platform together with an appropriate strategy to tackle the diffusion of obesity and other lifestyle-related illnesses among teenagers. Indeed, the design of an engaging strategy, leveraging a complementary set of technologies, is the approach proposed by the project to promote the adoption of healthy habits such as active lifestyle and balanced nutrition and to effectively counter-fight the emergence of overweight and obesity in the younger population. A technological key element of such a strategy sees the adoption of wearable sensors to monitor teenagers’ activities, which is at the basis of developing awareness about the current lifestyle. This paper describes the experience carried out in the framework of the PEGASO project in developing and evaluating wearable monitoring systems addressed to adolescents. The paper describes the methodological approach based on the co-designing of such a wearable system and the main results that, in the first phase, involved a total of 407 adolescents across Europe in a series of focus groups conducted in three countries for the requirements definition phase. Moreover, it describes an evaluation process of signal reliability during the usage of the wearable system. The main results described here are: (a) a prototype of the standardized experimental protocol that has been developed and applied to test signal reliability in smart garments; (b) the requirements definition methodology through a co-design activity and approach to address user requirements and preferences and not only technological specifications. Such co-design approach is able to support a higher system acceptance and usability together with a sustained adoption of the solution with respect to the traditional technology push system development strategy.