As shown three decades ago, in situations where the initial stresses before buckling are not negligible compared to the elastic moduli, the geometrical dependence of the tangential moduli on the initial stresses must be taken into account in stability analysis, and the stability or bifurcation criteria have different forms for tangential moduli associated with different choices of the finite strain measure. So it has appeared paradoxical that, for sandwich columns, different but equally plausible assumptions yield different formulas, Engesser’s and Haringx’ formulas, even though the axial stress in the skins is negligible compared to the axial elastic modulus of the skins and the axial stress in the core is negligible compared to the shear modulus of the core. This apparent paradox is explained by variational energy analysis. It is shown that the shear stiffness of a sandwich column, provided by the core, generally depends on the axial force carried by the skins if that force is not negligible compared to the shear stiffness of the column (if the column is short). The Engesser-type, Haringx-type, and other possible formulas associated with different finite strain measures are all, in principle, equivalent, although a different shear stiffness of the core, depending linearly on the applied axial load, must be used for each. The Haringx-type formula, however, is most convenient because it represents the only case in which the shear modulus of the core can be considered to be independent of the axial force in the skins and to be equal to the shear modulus measured in simple shear tests (e.g., torsional test). Extensions of the analysis further show that Haringx’s formula is preferable for a highly orthotropic composite because a constant shear modulus of the soft matrix can be used for calculating the shear stiffness of the column, and further confirm that Haringx’s buckling formula with a constant shear stiffness is appropriate for helical springs and built-up columns (laced or battened).