Accurately assessing people’s gait, especially in real-world conditions and in case of impaired mobility, is still a challenge due to intrinsic and extrinsic factors resulting in gait complexity. To improve the estimation of gait-related digital mobility outcomes (DMOs) in real-world scenarios, this study presents a wearable multi-sensor system (INDIP), integrating complementary sensing approaches (two plantar pressure insoles, three inertial units and two distance sensors). The INDIP technical validity was assessed against stereophotogrammetry during a laboratory experimental protocol comprising structured tests (including continuous curvilinear and rectilinear walking and steps) and a simulation of daily-life activities (SDA, including intermittent gait and short walking bouts). To evaluate its performance on various gait patterns, data were collected on 128 participants from seven cohorts: healthy young and older adults, patients with Parkinson’s disease, multiple sclerosis, chronic obstructive pulmonary disease, congestive heart failure, and proximal femur fracture. Moreover, INDIP usability was evaluated by recording 2.5-hours of real-world unsupervised activity. Excellent absolute agreement (ICC > 0.95) and very limited mean absolute errors were observed for all cohorts and DMOs (cadence ≤ 0.61 steps/min, stride length ≤ 0.02 m, walking speed ≤ 0.02 m/s) in the structured tests. Larger, but limited, errors were observed during the SDA (cadence 2.72–4.87 steps/min, stride length 0.04–0.06 m, walking speed 0.03–0.05 m/s). Neither major technical nor usability issues were declared during the 2.5-hours acquisitions. Therefore, the INDIP system can be considered a valid and feasible solution to collect reference data for analyzing gait in real-world conditions.