Systems and methods for dimensionally rating mail pieces including cards, letters, flats, mailers, packages and parcels using a pointing device such as a digital pen are described. In one illustrative configuration the system includes a digital pen, a three dimensional digital pen pattern device, a computer and a printer for printing evidence of postage payment. A mail piece such as a small parcel is placed on the opened three dimensional digital pen pattern device. The user may select a digital pen pattern command box or may otherwise engage or be prompted to begin measurements. For a rectangular parcel, the user selects a bottom right and then a top left measurement point. The system then calculates the dimensions of the parcel, dimensionally rates it and then accounts for and prints a corresponding postage indicium.