Adherence of patients to treatment and appropriateness of prescribed footwear are mandatory for successful prevention of Diabetic foot ulceration. In a Public Healthcare Service, footwear approval is under the responsibility of the clinician. In some cases kinetic measurements are taken inside the shoes to support the clinical decision; however, an overall agreement is still missing with respect to a simple, reliable and effective test protocol based on proper threshold values. Authors’ past experiences, specific needs of the Diabetic outpatient service, and suggestions from valuable literature led to an instrumental test protocol based on reference peak pressure (PP) thresholds and gait line (GL) specific for each level of risk. Permission was obtained for one preliminary validation session at the Authors’ outpatient service, during which 11 patients at high/very high risk of ulceration were examined—9 for testing new footwear, 2 for monitoring 12-month-old footwear. The protocol was well accepted by patients and operators, fast and easy to be used. Based on the instrumental, clinical and visual inspection data; 4 new footwear did not pass the test; 5 passed the test but integration or minor changes were requested; the 2 old footwear were found no more effective. As a first positive feedback, after 4 months of wearing the modified prescriptions none of the patients had developed plantar ulcers or signs of tissue damage. Successive data processing proved that in all patients altered PPs and deviated GLs did correlate with alterations of other kinetic parameters. The protocol, which is proved to be sensitive and valuable for the Diabetic foot care, may have a general validity; the delivered specific PP thresholds and reference data, instead, can be reliably used if the test is performed with a calibrated Pedar Insole System and with the wide Insoles in the range UW-YW (EU size 36 - 45).