Human faces captured in real-world conditions present large variations in shape and occlusions due to differences in pose, expression, use of accessories such as sunglasses and hats and interactions with objects (e.g. food). Current face landmark estimation approaches struggle under such conditions since they fail to provide a principled way of handling outliers. We propose a novel method, called Robust Cascaded Pose Regression (RCPR) which reduces exposure to outliers by detecting occlusions explicitly and using robust shape-indexed features. We show that RCPR improves on previous landmark estimation methods on three popular face datasets (LFPW, LFW and HELEN). We further explore RCPR’s performance by introducing a novel face dataset focused on occlusion, composed of 1,007 faces presenting a wide range of occlusion patterns. RCPR reduces failure cases by half on all four datasets, at the same time as it detects face occlusions with a 80/40% precision/recall.