Gait analysis has been widely studied by researchers due to the impact in clinical fields. It provides relevant information on the condition of a patient’s pathologies. In the last decades, different gait measurement methods have been developed in order to identify parameters that can contribute to gait cycles. Analyzing those parameters, it is possible to segment and identify different phases of gait cycles, making these studies easier and more accurate. This paper proposes a simple gait segmentation method based on plantar pressure measurement. Current methods used by researchers and clinicians are based on multiple sensing devices (e.g., multiple cameras, multiple inertial measurement units (IMUs)). Our proposal uses plantar pressure information from only two sensorized insoles that were designed and implemented with eight custom-made flexible capacitive sensors. An algorithm was implemented to calculate gait parameters and segment gait cycle phases and subphases. Functional tests were performed in six healthy volunteers in a 10 m walking test. The designed in-shoe insole presented an average power consumption of 44 mA under operation. The system segmented the gait phases and sub-phases in all subjects. The calculated percentile distribution between stance phase time and swing phase time was almost 60%/40%, which is aligned with literature reports on healthy subjects. Our results show that the system achieves a successful segmentation of gait phases and subphases, is capable of reporting COP velocity, double support time, cadence, stance phase time percentage, swing phase time percentage, and double support time percentage. The proposed system allows for the simplification of the assessment method in the recovery process for both patients and clinicians.