A novel resampling framework is proposed to evaluate the robustness and generalization capability of deep learning models with respect to distribution shift. We use Auto Encoder Variational Bayes to find a latent representation of the data, on which a Variational Gaussian Mixture Model is applied to deliberately create distribution shift by dividing the dataset into different clusters. Wasserstein distance is used to characterize the extent of distribution shift between the training and the testing data splits. We compare several conventional Convolutional Neural Network (CNN) architectures as well as Bayesian CNN models for image classification on the Fashion-MNIST dataset to assess their robustness under the deliberately created distribution shift.