The fundamental quasi-TE and quasi-TM modes of a sub-wavelength strip silicon waveguide are not purely TE or TM as the plane waves in free space. We investigate theoretically and experimentally the far-field polarization compositions of the two waveguide modes after they emanate from the waveguide facet. The measured polarization extinction ratios (PERs) of 31 dB for the quasi-TM mode and 26 dB for quasi-TE mode using free-space polarizers are consistent with our numerical analysis. Moreover, our far-field simulations show that the free-space measurement of PERs is influenced, and in many cases limited, by the sizes of various apertures in the experimental setup. This suggests a potential trade-off between achievable PERs and overall power detection/collection efficiency.