The accurate assessment of thrombus age in deep vein thrombosis (DVT) remains a clinical challenge with significant therapeutic implications. Patient history is unreliable, and recurrent DVT cannot be excluded in up to 30% of cases. Standard ultrasound offers high sensitivity for acute events but is limited in recurrent or chronic disease, where residual abnormalities persist for months. Recent imaging advances, including CT, MR venography, and direct thrombus imaging (MR-DTI), provide valuable tools for distinguishing acute from chronic thrombi. In particular, MR-DTI has demonstrated high accuracy in differentiating acute recurrent DVT from chronic residual findings without contrast and within a short acquisition time. This presentation reviews key imaging modalities, highlights evidence from multicenter studies, and discusses their role in guiding optimal therapeutic strategies.