The rhythmic control of the lower limb muscles influences the cycle-to-cycle variability during a walking task. The benefits of insoles, commonly used to improve the walking gait, have been little studied. Therefore, the aim of this study was to assess the walking gait variability and stability on different walking conditions (without shoes, WTS, with shoes, WS, with shoes and insoles, WSI) related to brain activity. Twelve participants randomly (WTS/WS/WSI) walked on a treadmill at 4 km/h for 10 min. Kinematic analysis (i.e., footstep and gait variability), brain activation (beta wave signal), rating of perceived exertion (RPE, CR-10 scale), and time domain measures of walking variability were assessed. The maximum Lyapunov exponent (LyE) on the stride cycle period’s datasets was also calculated. Stride length and cycle calculated for all walking conditions were 61.59 ± 2.53/63.38 ± 1.43/64.09 ± 2.40 cm and 1.11 ± 0.03/1.14 ± 0.03/1.15 ± 0.04 s (F_1,10 = 4.941/p = 0.01, F_1,10 = 4.938/p = 0.012) for WTS, WS, WSI, respectively. Beta wave (F_1,10 = 564.201/p = 0.0001) was higher in WTS compared to WS and WSI. Analysis of variance’s (ANOVA) LyE showed a F_1,10 = 3.209/p = 0.056, while post hoc analysis showed a significant effect between WS and WSI with p = 0.023, and nonsignificant effects between WTS and WS/WSI (p = 0.070/0.607), respectively. Small perturbations of the foot can influence the control of gait rhythmicity by increasing the variability in a dissipative deterministic regimen.