(1) Background: The development of a lightweight, easy-to-use system that measures the foot’s plantar pressure is becoming an increasingly important area of research in physiotherapy. For further development of the smart sock system, a formative usability study was conducted, where the smart textile sock sensor system was used for self-correction during functional tasks; (2) Methods: Five athletes from the football school participated in the formative usability study. Athletes performed pre-defined functional tasks for self-correction when interacting with the smart textile sock system. Formative usability evaluation methods: effectiveness (task success rate, error rate), efficiency (time-based), satisfaction evaluated by System Usability Scale (SUS); (3) Results: Formative usability indicators: task completeness effectiveness ranged from 40% to 100% in the first- and second-stage tasks. Completed task efficiency time: Stage 1, from 4.2 s (SD 1.3) to 88.8 s (SD 19.8); Stage 2, from 7.2 s (SD 1.9) to 9.6 s (SD 2.1). Satisfaction was assessed by the SUS system user group with 76 points (SD 7.42), which indicates “good” satisfaction; (4) Conclusions: formative usability indicators showed the need for technical improvements to the smart textile sock pressure sensor system. The SUS results indicate “good” satisfaction with the smart textile sock pressure sensor system and its application.