Matching images containing large viewpoint and viewing direction changes, resulting in large perspective differences, still is a very challenging problem. Affine shape estimation, orientation assignment and feature description algorithms based on detected hand crafted features have shown to be error prone. In this paper, affine shape estimation, orientation assignment and description of local features is achieved through deep learning. Those three modules are trained based on loss functions optimizing the matching performance of input patch pairs. The trained descriptors are first evaluated on the Brown dataset (Brown et al., 2011), a standard descriptor performance benchmark. The whole pipeline is then tested on images of small blocks acquired with an aerial penta camera, to compute image orientation. The results show that learned features perform significantly better than alternatives based on hand crafted features.