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 recess, a set of angled members, and an illumination device. The recess is disposed within the base and is sized such that a user's foot may be disposed within the recess. The illumination device is disposed on the base and is medially aligned with the recess. The illumination device is oriented so as to transmit an illumination output upward or perpendicular to the top surface of the base. The angled members include an angled top surface and are configured to reliably couple within the recess of the base. A second embodiment of the present invention relates to a method of encouraging correct knee and ankle alignment in an article of footwear.