In this paper, we describe the design journey of a smart clothing system, SoPhy from the research laboratory to finally being evaluated in the hospital setting. SoPhy is a smart socks-based system, designed to make physiotherapy video consultations effective for assessing lower limb issues. SoPhy is the result of a 3-year journey of development, study and refinement of a research prototype done in collaboration with a physiotherapist. Drawing on this journey, we present seven lessons that emphasize on the importance of fostering strong collaborations with clinicians to move beyond laboratory studies and reach the target health setting. We provide contextual narratives on how we designed a comfortable smart clothing for patients; how we created an intuitive mapping of sensor data for clinicians; how we integrated hospital practice in the system design, and how we managed the ethics clearance for the field evaluation. We hope that these lessons are useful for HCI and health researchers who aim to innovate the field of health but feel restricted with the little knowledge of design and electronics.