The increase in population life expectancy poses growing challenges in terms of care, autonomy, and quality of life. Although wearable technologies have demonstrated significant potential in health and social care, many current solutions remain closed, rigid systems that poorly accommodate the functional and technological diversity of older users. This paper presents the design of a product-service concept built upon a modular technological ecosystem that integrates multiple wearable devices, fixed sensors, hybrid connectivity, and a control application. The system is conceived to accommodate a wide range of user profiles in both domestic and community settings. The system architecture follows the IoT Thing–Cloud–App model, structured using the Cosica methodology, and enables the progressive integration of devices according to user needs. The primary wearable acts as the central node, managing connectivity contextually via Bluetooth or 4G. An application—envisioned in differentiated versions for users and caregivers—provides an accessible platform for supervision and configuration, aiming to reduce uncertainty and preserve the perception of control. The cloud infrastructure supports data synchronisation and remote services, and is being designed to enable the future integration of AI-based analytics for early detection and intervention. This proposal addresses key challenges at the intersection of ageing and technology, including variations in technological literacy and cognitive capacity—towards more inclusive, flexible, and user-aligned technologies. Beyond the system concept, the work seeks to advance methodological approaches to the design of technological ecosystems and offers insights into relevant design considerations for ageing populations.