Gait analysis allows clinicians and researchers to quantitatively characterize the kinematics and kinetics of human movement. Devices that quantify gait can be either portable, such as instrumented shoes, or non-portable, such as motion capture systems and instrumented walkways. There is a tradeoff between these two classes of systems in terms of portability and accuracy. However, recent computer advances allow for the collection of meaningful data outside of the clinical setting. In this work, we present the DeepSole system combined with the different neural network models. This system is a fully capable to characterize the gait of the individuals and provide vibratory feedback to the wearer. Thanks to the flexible construction and its wireless capabilities, it can be comfortably worn by wide arrange of people, both able-bodied and people with pathologies that affect their gait. It can be used for characterization, training, and as an abstract sensor to measure human gait in real-time. Three neural network models were designed and implemented to map the sensors embedded in the DeepSole system to gait characteristics and events. The first one is a recurrent neural network that classifies the gait into the correct gait phase of the wearer. This model was validated with data from healthy young adults and children with Cerebral Palsy. Furthermore, this model was implemented in real-time to provide vibratory feedback to healthy young adults to create temporal asymmetry on the dominant side during regular walking. During the experiment, the subjects who walked had an increased stance time on both sides, but the dominant side was affected more. The second model is encoder-decoder recurrent neural network that maps the sensors into current gait cycle percentage. This model is useful to provide continuous feedback that is synchronized to the gait. This model was implemented in real-time to provide vibratory feedback to six muscle groups used during regular walking. The effects of the vibration were analyzed. It was found that depending on the feedback, the subjects changed their spatial and temporal gait parameters. The third model uses all the sensors in the instrumented footwear to identify a motor phenomenon called freezing of gait in patients with Parkinson’s Disease. This phenomenon is characterized by transient periods, usually lasting for several seconds, in which attempted ambulation is halted. The model has better performance than the state-of-the-art and does not require any pre-processing. The DeepSole system when used in conjunction with the presented models is able to characterize and provide feedback in a wide range of scenarios. The system is portable, comfortable, and can accommodate a wide range of populations who can benefit from this wearable technology.