This study aimed to systematically review and summarize the available data regarding the influence of overweight and obesity across the lifespan on obstacle crossing during walking. Four databases were systematically searched with no limitation on publication date following the Cochrane Handbook for Systematic Reviews and PRISMA guidelines. Only full-text English-language articles published in a peer-reviewed journal were eligible. They had to compare obstacle crossing during walking by overweight or obese individuals with individuals of normal body weight. Five studies were considered eligible. All the studies assessed kinematics; only one assessed kinetics, but none investigated muscle activity or obstacle contact. Compared to normal individuals crossing obstacles, overweight or obese individuals exhibited lower velocity, shorter step length, lower cadence, and less time spent in single-limb support. They also exhibited increased step width, more time spent in double support, and greater trailing leg ground force reaction and centre of mass acceleration. Overall, the small number of included studies did not allow us to draw any conclusions. However, being overweight or obese seems to have a potentially negative influence on the kinematics of gait parameters due to a tendency to trip, fall, and suffer severe fall-related injuries when negotiating obstacles on foot in real-life environments.