Foot and ankle instability can be seen both in acute and chronic settings, and isolating the diagnosis can be difficult. Imaging can contribute to the clinical presentation not only by identifying abnormal morphology of various supporting soft tissue structures but also by providing referring clinicians with a sense of how functionally incompetent those structures are by utilizing weight-bearing images and with comparison to the contralateral side. Loading the affected joint and visualizing changes in alignment provide clinicians with information regarding the severity of the abnormality and, therefore, how it should be managed.