Background: Foot problems are common in older people, however the contribution of incorrectly fitting footwear and heel elevation to the development of foot pain and deformity has not been fully evaluated. Objectives: To examine the relationship between footwear characteristics and the prevalence of common forefoot problems in older people. Methods: Presence of foot pain and deformity were identified in 176 people (56 men and 120 women) aged 62–96 years (mean 80.09, SD 6.42) using a questionnaire and clinical assessment. Shoe fit was determined by comparing length, width and area measurements of shoes with foot measurements. Past and present use of high heels in women was documented, and heel elevation of footwear was measured. Results: Most subjects wore shoes narrower than their feet. Women wore shoes that were shorter, narrower and had a reduced total area compared to their feet than men. Wearing shoes substantially narrower than the foot was associated with corns on the toes, hallux valgus deformity and foot pain, whereas wearing shoes shorter than the foot was associated with lesser toe deformity. Wearing shoes with heel elevation greater than 25 mm was associated with hallux valgus and plantar calluses in women. Conclusion: Incorrectly fitting footwear is common in older people and is strongly associated with forefoot pathology and foot pain. These findings highlight the need for footwear assessment in the management of foot problems in older people.