The stylohyoid complex (SHC) plays a central role in the anatomical and functional relationships between styloid process (SP), hyoid bone, and adjacent neurovascular structures. Identification of physiologic variants from pathology is crucial, particularly as SP elongation—previously considered abnormal if more than 30 mm—is found in asymptomatic individuals. Dynamic factors such as neck mobility also complicate assessment, with high-definition imaging thereby becoming required. While panoramic radiography is a primary screen, computed tomography (CT) remains the gold standard to determine SP form and spatial relationship to neurovascular structures. Emerging data emphasize the importance of angulation and proximity of the SP to vascular elements as more determinative than length in the diagnosis of SHC-related syndromes. Techniques like angio-CT and Doppler ultrasonography enhance the diagnostic sensitivity through illustrations of dynamic compression of the vessels, such as in styloid jugular nutcracker syndromes and stylo-carotid syndromes. A multimodal, dynamic approach to imaging is therefore imperative for complete assessment and accurate diagnosis of SHC pathologies.