To calculate the stresses in soil caused by surface loading, the well-known analytical equations of Boussinesq and Westergaard (in the case of thin rigid varved layers) are frequently utilized. Nevertheless, the existing formulations consist of certain limitations. This present study showcases the impact of analytical (theoretical) determinations of stress distribution as compared to experimental ones (i.e., pressure cells) by considering existing literature data. For the case of unreinforced soils, the theoretical stress was calculated using the Boussinesq equation. Westergaard equation was used for the case of geosynthetic reinforced soils having different rigidity (i.e., tensile stiffness) of multi-layer reinforcements. Irrespective of unreinforced and reinforced cases, the analytical formulations gave much lesser values as compared to the experimental findings. However, the percentage of variation of theoretical findings as compared to experimental is lesser for the case of reinforced soils having higher rigidity reinforcement as compared to lesser rigidity. It could be due to the lesser lateral displacements of soil for the case of higher rigidity of reinforcements, the Westergaard equation shows good agreement.