Systems and methods for fitting a wearable heads-up display (WHUD) to a subject are described. Imaging data representative of at least a portion of the subject's head with one or more gaze positions of the eyes is obtained from a plurality of cameras. One or more models representative of the subject's head are generated and a set of features is recognized in the one or more models. One or more models of the WHUD are also obtained based on WHUD data stored in memory. One or more simulations are performed positioning one or more WHUD models in proximity to at least one subject model based at least in part on the set of features recognized in the subject model. A fit of a WHUD to the subject is evaluated based at least in part on a determination regarding whether the simulation satisfies one or more of a set of criteria.