An increase in plantar pressure and skin temperature is commonly associated with an increased risk of diabetic foot ulcers. However, the effect of insoles in reducing plantar temperature has not been commonly studied. The aim was to assess the effect of walking in insoles with different features on plantar temperature. Twenty-six (F/M:18/8) participants—13 with diabetes and 13 healthy, aged 55.67 ± 9.58 years—participated in this study. Skin temperature at seven plantar regions was measured using a thermal camera and reported as the difference between the temperature after walking with an insole for 20 m versus the baseline temperature. The mixed analyses of variance indicated substantial main effects for the Insole Condition, for both the right [Wilks’ Lambda = 0.790, F(14, 492) = 4.393, p < 0.01, partial eta squared = 0.111] and left feet [Wilks’ Lambda = 0.890, F(14, 492) = 2.103, p < 0.011, partial eta squared = 0.056]. The 2.5 mm-tall dimple insole was shown to be significantly more effective at reducing the temperature in the hallux and third met head regions compared to the 4 mm-tall dimple insole. The insoles showed to be significantly more effective in the diabetes group versus the healthy group, with large effect size for the right [Wilks’ Lambda = 0.662, F(14, 492) = 8.037, p < 0.000, Partial eta-squared = 0.186] and left feet [Wilks’ Lambda = 0.739, F(14, 492) = 5.727, p < 0.000, Partial eta-squared = 0.140]. This can have important practical implications for designing insoles with a view to decrease foot complications in people with diabetes.