Background: Plantar heel pain is a common foot disorder aggravated by weight-bearing activity. Despite considerable focus on therapeutic interventions such as orthoses, there has been limited investigation of footwear-related issues in people with plantar heel pain. The aim of this study was to investigate whether people with plantar heel pain experience footwear-related difficulties compared to asymptomatic individuals, as well as identifying factors associated with footwear comfort, fit and choice. Methods: The footwear domain of the Foot Health Status Questionnaire (FHSQ) was assessed in 192 people with plantar heel pain and 69 asymptomatic controls. The plantar heel pain group was also assessed on a variety of measures including: foot posture, foot strength and flexibility, pedobarography and pain level. A univariate analysis of covariance, with age as the covariate, was used to compare the heel pain and control groups on the FHSQ footwear domain score. A multiple regression model was then constructed to investigate factors associated with footwear scores among participants with plantar heel pain. Results: When compared to asymptomatic participants, people with plantar heel pain reported lower FHSQ footwear domain scores (mean difference -24.4; p < 0.001; 95 % CI: -32.0 to -17.0). In the participants with heel pain, footwear scores were associated with maximum force beneath the postero-lateral heel during barefoot walking, toe flexor strength and gender. Conclusions: People with plantar heel pain experience difficulty with footwear comfort, fit and choice. Reduced heel loading during barefoot walking, toe flexor weakness and female gender are all independently associated with reports of footwear difficulties in people with heel pain. Increased focus, in both clinical and research settings, is needed to address footwear-related issues in people with plantar heel pain.