Background: Adequate compliance with wearing therapeutic footwear (TF) to prevent diabetic foot ulcers is known to be low. The primary aim of this study was to identify population awareness about the ulceration and/or recurrence risk according to footwear choice. The secondary aim was to evaluate the compliance level in footwear choice based on a patient’s own risk. Methods: Forty podiatrists participated from 1 September 2017 to 31 August 2018, providing six-section forms which included personal data, risk classification, footwear characteristics and a knowledge questionnaire. Results: This study included 1507 patients. Those with active ulcers were excluded. A total of 43% of patients belonged to risk class 0, 19% to risk class 1, 19% to risk class 2 and 19% to risk class 3. A total of 58% had foot deformities. Conclusions: Nearly half of patients with a high risk of ulceration had knowledge of their own risk but the majority of them did not follow the recommendations. Only a small percentage (36%) of risk class 3 patients wore footwear suitable for their risk class. There was poor consideration of footwear choice among patients. We highlight critical issues in patient education and compliance with wearing footwear appropriate to their risk class.