Patients with symptoms from compression of the neurovascular bundle in the thoracic outlet are described as having thoracic outlet syndrome (TOS), which is best thought of as three conditions classified according to which structures are involved. The purpose of this article is to review the role of imaging in evaluation of patients with TOS, beginning with diagnosis and extending through postoperative management. While diagnosis of TOS still rests on the patient’s presenting history and physical examination, imaging examinations are helpful in supporting the diagnosis, delineating abnormal anatomy, determining which structures are compressed, identifying the site of compression, and excluding other diagnoses. Magnetic resonance imaging is the noninvasive imaging modality of choice in evaluating patients with suspected TOS, but computed tomography also plays an important role, particularly in delineating bone anatomy. Evidence of vascular damage is required to make the diagnosis of TOS at imaging. Dynamic compression of the axillosubclavian vessels at the thoracic outlet can be a finding supportive of the diagnosis of TOS but is not a stand-alone diagnostic criterion, as it can be seen in patients without TOS. As diagnosis and treatment of TOS increase, radiologists will increasingly encounter the TOS patient after decompression surgery. Recognition of the expected postoperative appearance of these patients is critical, as is an understanding of the imaging findings of potential short- and long-term complications.