This cross-sectional observational study is to reveal what kind of gait feature is relevant to elevated segment and its plantar pressure for prevention of diabetic foot ulcers. In 57 diabetic patients, the relationship between elevated plantar pressure and gait features was analyzed. To conduct this investigation, a simultaneous measurement system of plantar pressure and gait features was constructed. Plantar pressure distribution was measured by F-scan with customized footwear, and gait features were mainly measured using wireless motion sensors attached to the sacrum and feet. Several gait features of small rolling during the mid-stance phase were relevant to the elevated plantar pressure.