We present an automated segmentation method based on the analysis of plantar pressure signals recorded from two synchronized wireless foot insoles. Given the strict limits on computational power and power consumption typical of wearable electronic components, our aim is to investigate the capability of a Hidden Markov Model machine-learning method, to detect gait phases with different levels of complexity in the processing of the wearable pressure sensors signals. Therefore three different datasets are developed: raw voltage values, calibrated sensor signals and a calibrated estimation of total ground reaction force and position of the plantar center of pressure. The method is tested on a pool of 5 healthy subjects, through a leave-one-out cross validation. The results show high classification performances achieved using estimated biomechanical variables, being on average the 96%. Calibrated signals and raw voltage values show higher delays and dispersions in phase transition detection, suggesting a lower reliability for online applications.