Wearable sensors could facilitate point of care, clinically feasible assessments of dynamic stability and associated fall risk through an assessment of single-task (ST) and dual-task (DT) walking. This study investigated gait changes between ST and DT walking and between older adult prospective fallers and non-fallers. The results were compared to a study based on retrospective fall occurrence. Seventy-five individuals (75.2 ± 6.6 years; 47 non-fallers, 28 fallers; 6 month prospective fall occurrence) walked 7.62 m under ST and DT conditions while wearing pressure-sensing insoles and accelerometers at the head, pelvis, and on both shanks. DT-induced gait changes included changes in temporal measures, centre of pressure (CoP) path stance deviations and coefficient of variation, acceleration descriptive statistics, Fast Fourier Transform (FFT) first quartile, ratio of even to odd harmonics, and maximum Lyapunov exponent. Compared to non-fallers, prospective fallers had significantly lower DT anterior–posterior CoP path stance coefficient of variation, DT head anterior–posterior FFT first quartile, ST left shank medial–lateral FFT first quartile, and ST right shank superior maximum acceleration. DT-induced gait changes were consistent regardless of faller status or when the fall occurred (retrospective or prospective). Gait differences between fallers and non-fallers were dependent on retrospective or prospective faller identification.