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Poorly fitting footwear has frequently been cited as an etiologic factor in the pathway to diabetic foot ulceration. However, we are unaware of any reports in the medical literature specifically measuring shoe size versus foot size in this high-risk population. We assessed the prevalence of poorly fitting footwear in individuals with and without diabetic foot ulceration. We evaluated the shoe size of 440 consecutive patients (94.1% male; mean ± SD age, 67.2 ± 12.5 years) presenting to an interdisciplinary teaching clinic. Of this population, 58.4% were diagnosed as having diabetes, and 6.8% had active diabetic foot ulceration. Only 25.5% of the patients were wearing appropriately sized shoes. Individuals with diabetic foot ulceration were 5.1 times more likely to have poorly fitting shoes than those without a wound (93.3% versus 73.2%; odds ratio [OR], 5.1; 95% confidence interval [CI], 1.2–21.9; P = .02). This association was also evident when assessing only the 32.3% of the total population with diabetes and loss of protective sensation (93.3% versus 75.0%; OR, 4.8; 95% CI, 1.1–20.9; P = .04). Poorly fitting shoes seem to be more prevalent in people with diabetic foot wounds than in those without wounds with or without peripheral neuropathy. This implies that appropriate meticulous screening for shoe-foot mismatches may be useful in reducing the risk of lower-extremity ulceration. (J Am Podiatr Med Assoc 96(4): 290–292, 2006)