Systems and methods are provided for a head-wearable device. The head-wearable device can include a display, a retractable side strap, and a housing. The housing includes an anchor point, an adjustment mechanism configured to change an exposed length of the retractable side strap, and a cable. The cable includes a first end and a second end coupled the cable-spooling portion of the adjustment mechanism and an intermediary portion of the cable that travels around the anchor point and is coupled to the retractable side strap. The cable is maintained at a predetermined tension by at least the adjustment mechanism or the anchor point. When the adjustment mechanism is adjusted, the cable winds/unwinds around the first or second cable-spooling portion of the adjustment mechanism, adjusting the exposed length of the retractable side strap to accommodate for different head sizes for users of the head-wearable device.