We numerically investigate nonlinear self-polarization flipping in a silicon waveguide. We identify specific silicon waveguide geometries that enhance this effect to facilitate its fabrication and experimental demonstration by varying various parameters such as fabrication distortion, waveguide loss, dispersion and laser noise to design the silicon waveguide. In optimized waveguides, we show that nonlinear self-polarization flipping can be observed with few tens of watts peak power pulses with widths as short as 60 ps and laser noise level as large as 7%.