Stress analysis is often necessary in the design of foundations of all types of structures, particularly buildings, retaining structures, dams, highway pavements, and embankments. In this chapter, the mathematical definitions of stress and strain and the elasticity of an isotropic material are first treated. This is followed by the classical theory of Boussinesq for the stress in a semi-infinite, elastic, isotropic, and homogeneous continuum loaded normally on its upper plane surface by a concentrated load. The Boussinesq solution is later extended to analyze the stresses produced by a uniformly distributed load over a flexible circular foundation, rectangular loading, strip loading, line loading, triangular loading, and embankment loading. The case of irregular loading using the Newmark's Chart is also considered. The settlement of a foundation under external loadings by the use of both the Boussinesq theory and the semi-empirical strain influence factor method proposed by Schmertmann et al. (1978) are considered.