A footwear measuring apparatus includes a body, a plurality of probes, one or more measurement devices and at least one calibration sensor. The plurality of probes are configured to extend from the body. The measurement devices are configured to measure distances that the plurality of probes extend from the body, wherein the distances indicate fit parameters of footwear. The at least one calibration sensor is configured to determine if the footwear measuring apparatus is properly positioned inside of the footwear for measuring.