Cardiovascular disease is one of the leading causes of death, representing 32% of all global deaths. The mainstay treatments are medical compression stockings (MCS) and physical activity. Although MCS has been shown to positively affect treatment and support disorder control (e.g. leg swelling), research shows incredibly low therapy compliance. Throughout history, the involvement of digital technologies has greatly enhanced healthcare. Nonetheless, developments are not embraced by the medical compression stockings industry yet. For instance, since the invention of medical compression stockings (with a graduated compression) in 1960, the design of medical compression stockings (MCS) has hardly changed. This thesis explores the integration of sensors into medical compression stockings and aims to innovate current compression stockings by including wearable technology. The feasibility and viability of smart stockings are examined, and barriers are defined through a combination of interviews, literature and user observations. Findings are translated into design requirements. Throughout the research, multiple problems have been identified, ranging from user dissatisfaction to product shortcomings. For instance, MCS only have an expected lifespan of half a year. Yet, MCS are yearly reimbursed by health insurance companies. Also, wearing, product care, and health complications can even shorten the lifespan of MCS. For the successful treatment of disorders, it is essential that MCS exert the correct amount of compression. The presented smart stockings with the app address these shortcomings. The smart stocking is able to monitor the exerted compression of MCS. By constantly validating the product, users gain ownership over the quality of their compression therapy. Aside from product validation, compression monitoring is translated into the level of fitness of the user. Increased compression (outside of the walking range) indicates an expanding circumference of the ankle. Together with a vascular surgeon, guidelines are discussed. The combination of the smart stocking and the app has the potential to give medical recommendations to users. With the app, users can be rewarded for their therapy adherence and goals tailored to the specific user and their physical capabilities. Lastly, not every healthcare complication is immediately measurable through compression change. Therefore, the app can ask additional questions based on visible signs, this way it also coaches users to monitor their health.