Appropriate choice of shoes with required cushioning characteristics is rather an urgent problem for people from very different groups, such as sportsmen, elderly people, people with foot disorders and locomotion problems. Present research is devoted to further development of wireless DAids™ Pressure Sock System and its application for shoe cushioning estimation. In particular, a new version of pressure sensors with improved sensitivity and working range is designed and tested. Based on above-mentioned developments, the possibility of shoe cushioning testing using DAid™ Pressure Sock System was studied. For this purpose, gait records of several test subjects who used sets of shoes with different cushioning properties, as well as bare walking, were made. Data analysis showed that the developed system gives the possibility to recognize different shoe cushioning. Several approaches to data processing to increase the sensitivity of such recognition are discussed. The comparison showed the potential ability of the developed system to test wirelessly shoe cushioning in real outdoor conditions. Such ability also provides the possibility to monitor and estimate degradation of cushioning quality of shoes under deterioration and environment.