Foot-related problems are prevalent across the globe, and this issue is aggravated by the presence of diabetes mellitus. Diabetic-foot-related issues include extreme foot pain, plantar corns, and diabetic foot ulcers. To assess these conditions, accurate characterization of plantar pressure is required. In this work, an in-shoe, low-cost, and multi-material pressure measuring insole, based on a piezoresistive material, was developed. The device has a high number of sensors, and was tested on 25 healthy volunteers and 25 patients with different degrees of diabetes. The working range of the device was observed to be 5 kPa to 900 kPa, with an average hysteresis error of 3.25%. Plantar pressure was found to increase from healthy to diabetic volunteers, in terms of both standing and walking. In the case of the diabetic group, the-high pressure contact area was found to strongly and positively correlate (R2 = 0.78) with the peak plantar pressure. During the heel strike phase, the diabetic volunteers showed high plantar pressure on the medial heel region. In regard to the toe-off phase, the central forefoot was found to be a prevalent site for high plantar pressure across the diabetic volunteers. The developed device is expected not only to assist in the prediction of diabetic ulceration or re-ulceration, but also to provide strategies and suggestions for foot pressure alleviation and pain mitigation.