Wearable devices as medical technologies are becoming an integral part of our lives. Many research studies are dedicated to these devices and are mainly focused on providing personal analytics, measuring physical status, and acquiring physiological signals and parameters. These continuously evolving technologies play an important role in telemedicine. Telemedicine can be broadly defined as the use of advanced telecommunications technologies to support many medical activities, such as the diagnosis, the analysis of patient data, the improvement of disease management and the treatment in remote areas. In this article, we present ATTICUS (Ambient-intelligent Tele-monitoring and Telemetry for Incepting and Catering over hUman Sustainability), an innovative remote monitoring system for ambient-assisted living based on the analysis of vital and behavioral parameters. The ATTICUS system consists of two essential components: a smart wearable—in the form of a short singlet—made of innovative textile which allows the acquisition of real-time body signals, e.g., electrocardiogram (ECG), breathing wave, temperature, and a multi-level Decision Support System (DSS), a distributed software which integrates advanced machine learning methods to automatically detect anomalies. ATTICUS is capable of operating in different application scenarios. Especially, the system will support in-home and out-home monitoring, personal check-ups, and specialized check-ups. Thus, the system will positively impact the canonical medical practices allowing simultaneous and continuous monitoring of a large number of people.