A new, continuously-monitoring portable device that monitors the diabetic foot has shown to help in reduction of diabetic foot complications. Persons affected by diabetic foot have shown to be particularly sensitive in the plantar surface; this sensitivity coupled with certain ambient conditions may cause dry skin. This dry skin leads to the formation of fissures that may eventually result in a foot ulceration and subsequent hospitalization. This new device monitors the micro-climate temperature and humidity areas between the insole and sole of the footwear. The monitoring system consists of an array of ten sensors that take readings of relative humidity within the range of 100% ± 2% and temperature within the range of −40 °C to 123.8 ± 0.3 °C. Continuous data is collected using embedded C software and the recorded data is processed in Matlab. This allows for the display of data; the implementation of the iterative Gauss-Newton algorithm method was used to display an exponential response curve. Therefore, the aim of our system is to obtain feedback data and provide the critical information to various footwear manufacturers. The footwear manufactures will utilize this critical information to design and manufacture diabetic footwear that reduce the risk of ulcers in diabetic feet.