At airports, security screening can cause long delays. In order to speed up screening a solution to avoid passengers removing their shoes to have them X-ray scanned is required. To detect threats or contraband items hidden within the shoe, a method of screening using frequency swept signals between 15 to 40 GHz has been developed, where the scan is carried out whilst the shoes are being worn. Most footwear is transparent to microwaves to some extent in this band. The scans, data processing and interpretation of the 2D image of the cross section of the shoe are completed in a few seconds. Using safe low power UWB radar, scattered signals from the shoe can be observed which are caused by changes in material properties such as cavities, dielectric or metal objects concealed within the shoe. By moving the transmission horn along the length of the shoe a 2D image corresponding to a cross section through the footwear is built up, which can be interpreted by the user, or automatically, to reveal the presence of concealed threat within the shoe. A prototype system with a resolution of 6 mm or less has been developed and results obtained for a wide range of commonly worn footwear, some modified by the inclusion of concealed material. Clear differences between the measured images of modified and unmodified shoes are seen. Procedures for enhancing the image through electronic image synthesis techniques and image processing methods are discussed and preliminary performance data presented.