Diabetic foot ulcers (DFUs) are a life-changing complication of diabetes that can lead to amputation. There is increasing evidence that long-term management with wearables can reduce incidence and recurrence of this condition. Temperature asymmetry measurements can alert to DFU development, but measurements of dynamic information, such as rate of temperature change, are under investigated. We present a new wearable device for temperature monitoring at the foot that is personalised to account for anatomical variations at the foot. We validate this device on 13 participants with diabetes (no neuropathy) (group name D) and 12 control participants (group name C), during sitting and standing. We extract dynamic temperature parameters from four sites on each foot to compare the rate of temperature change. During sitting the time constant of temperature rise after shoe donning was significantly (p < 0.05) faster at the hallux (p = 0.032, 370.4 s (C), 279.1 s (D)) and 5th metatarsal head (p = 0.011, 481.9 s (C), 356.6 s (D)) in participants with diabetes compared to controls. No significant differences at the other sites or during standing were identified. These results suggest that temperature rise time is faster at parts of the foot in those who have developed diabetes. Elevated temperatures are known to be a risk factor of DFUs and measurement of time constants may provide information on their development. This work suggests that temperature rise time measured at the plantar surface may be an indicative biomarker for differences in soft tissue biomechanics and vascularisation during diabetes onset and progression.