One embodiment of the present invention relates to a footwear characteristic measuring system designed to determine measurements of a particular footwear wedge insert which may be used to encourage correct knee alignment in an article of footwear. The system includes a base, a stepped member, a platform, and an illumination system. The stepped member or piano hinge is positioned on the top surface of the base adjacent to or partially under the platform. The platform is disposed above the top surface of the base and connected on a first side to the base via a hinge. A second portion of the platform is positioned on top of a portion of the stepped member so as to form a particular angle with respect to the base depending on the height of the particular stepped member surface. The illumination system is oriented to transmit an illumination output upward or perpendicular to the top surface of the base.