Diabetic peripheral neuropathy (DPN) is a common complication leading to foot ulceration and amputation. Several kinematic, kinetic and plantar pressure measures have been proposed for DPN detection, however findings have been inconsistent. In this work, we present new shape features that capture variations in the plantar pressure using shape and entropy measures to the study of patients with retinopathy, DPN and nephropathy, and a control diabetic group with no complications. The change in the peak plantar pressure (PPP) position with each step for both feet was represented as a convex polygon, asymmetry index, area of the convex polygon, 2nd wavelet moment (WM2) and sample entropy (SamEn). WM2 and the SamEn were more sensitive in capturing variations due to presence of complications than the area and asymmetry measures. WM2 of the left heel (median: 1st IQ, 3rd IQ): 8.27 (4.6,14.8) and left forefoot: 9.2 (2.4,16) were significantly lower for the DPN group compared to the control (CONT) group (heel 11.9 (5.0,16.4); forefoot: 10.3 (4.4,21.3), p'<'0.05). SamEn for the DPN group was significantly lower in the right foot compared to the left foot (1.3 (1.26, 1.37) and 1.33 (1.26,1.4), p'<'0.01) compared to CONT (right foot: 1.37 (1.24,1.45) and left foot: 1.34 (1.25,1.42), P'<'0.05). These new shape and regularity features have shown promising results in detecting diabetic peripheral neuropathy and warrant further investigation.