The goal of this paper is to generalize results concerning the deformation theory of Calabi-Yau and Fano threefolds with isolated hypersurface singularites, due to the first author, Namikawa and Steenbrink. In particular, under the assumption of terminal singularities, Namikawa proved smoothability in the Fano case and also for generalized Calabi-Yau threefolds assuming that a certain topological first order condition is satisfied. In the case of dimension 3, we extend their results by, among other things, replacing terminal with canonical. In higher dimensions, we identify a class of singularities to which our method applies. A surprising aspect of our study is the role played by the higher Du Bois and higher rational singularities, recently introduced by Mustat ¸ȃ, Popa, Saito and their coauthors. While the results in this paper only require the notion of 1rational and 1-Du Bois singularities, we also consider the case of k-rational and k-Du Bois isolated hypersurface singularities for k ≥ 1, which is of independent interest. In particular, we propose a general definition for k-rational singularities and show that it agrees with the previous definition in the case of isolated hypersurface singularities. Among other deformation theoretic results in higher dimensions, we obtain smoothing results for generalized Fano varieties whose singularities are not 1-rational, and for generalized Calabi-Yau varieties whose singularities are not 1-rational but are 1-Du Bois under a topological condition on the links which is similar to the first order obstruction in dimension 3.