The spectrum of venous thromboembolic (VTE) disease encompasses both acute deep venous thrombosis (DVT) and chronic postthrombotic changes (CPC). A large percentage of acute DVT patients experience recurrent VTE despite adequate anticoagulation, and may progress to CPC. Further, the role of iliocaval venous obstruction (ICVO) in lower-extremity VTE has been increasingly recognized in recent years. Imaging continues to play an important role in both acute and chronic venous disease. Venous duplex ultrasound remains the gold standard for diagnosing acute VTE. However, imaging of CPC is more complex and may involve computed tomography, magnetic resonance, contrast-enhanced ultrasound, or intravascular ultrasound. In this narrative review, we aim to discuss the full spectrum of venous disease imaging for both acute and chronic venous thrombotic disease.