A system and method of detecting display fit measurements and/or ophthalmic measurements for a head mounted wearable computing device including a display device is provided. The system and method may include capturing image data including a face of a user to be fitted for the head mounted wearable computing device. A three-dimensional head pose and gaze measurements may be extracted and a three-dimensional model may be developed from the captured image data. The system may detect display fit measurements and/or ophthalmic fit measurements from the three-dimensional model, and may provide one or more head mounted wearable computing devices that meet the display fit and/or ophthalmic fit requirements.