Walking remains a highly recommended form of exercise for the management of obesity. Thus, comfortable and adequate shoes represent, together with the prescription of a safe adapted physical activity, an important means to achieve the recommended physical activity target volume. However, the literature on shoes specific for obese individuals is inadequate. The aim of the present study was to compare the performance of shoes specifically designed for subjects with obesity with everyday sneakers during instrumented 6-min walking test and outdoor 30-min ambulation in a group of subjects with obesity using a single wearable device. Twenty-three obese individuals (mean age 58.96 years) were recruited and classified into two groups: deconditioned (n = 13) and non-deconditioned patients (n = 10). Each participant was evaluated with his/her daily sneakers and the day after with shoes specifically designed for people with obesity by means of a questionnaire related to the comfort related to each model of shoes and instrumentally during the i6MWT and an outdoor walking test. The results showed that the specifically designed shoes displayed the higher score as for comfort, in particular in the deconditioned group. During the i6MWT, the distance walked, and step length significantly increased in the deconditioned group when specifically designed shoes were worn; no significant changes were observed in the non-deconditioned individuals. The deconditioned group displayed longer step length during the outdoor 30-min ambulation test. In the non-deconditioned group, the use of specific shoes correlated to better performance in terms of gait speed and cadence. These data, although preliminary, seem to support the hypothesis that shoes specifically conceived and designed for counteracting some of the known functional limitations in subjects with obesity allow for a smoother, more stable and possibly less fatiguing gait schema over time.