In this paper, we present a method of clothes retargeting; generating the potential poses and deformations of a given 3D clothing template model to fit onto a person in a single RGB image. The problem is fundamentally ill-posed as attaining the ground truth data is impossible, i.e., images of people wearing the different 3D clothing template model at exact same pose. We address this challenge by utilizing large-scale synthetic data generated from physical simulation, allowing us to map 2D dense body pose to 3D clothing deformation. With the simulated data, we propose a semi-supervised learning framework that validates the physical plausibility of the 3D deformation by matching with the prescribed body-to-cloth contact points and clothing silhouette to fit onto the unlabeled real images. A new neural clothes retargeting network (CRNet) is designed to integrate the semi-supervised retargeting task in an end-to-end fashion. In our evaluation, we show that our method can predict the realistic 3D pose and deformation field needed for retargeting clothes models in real-world examples.