Walking is often cited as the best form of activity for persons over the age of 60. In this paper we outline the development and evaluation of a smart garment system that aims to monitor the wearer's wellbeing and activity regimes during walking activities. Functional requirements were ascertained using a combination of questionnaires and two workshops with a target cohort. The requirements were subsequently mapped onto current technologies as part of the technical design process. In this paper we outline the development and second round of evaluations of a prototype as part of a three-phase iterative development cycle. The evaluation was undertaken with 6 participants aged between 60 and 73 years of age. The results of the evaluation demonstrate the potential role that technology can play in the promotion of activity regimes for the older population.