Surface-Enhanced Raman Scattering (SERS) is an advanced analytical technique renowned for its heightened sensitivity in detecting molecular vibrations. Its integration into wearable technologies facilitates the monitoring of biofluids, such as sweat and tears, enabling continuous, non-invasive, real-time analysis of human chemical and biomolecular processes. This capability underscores its significant potential for early disease detection and the advancement of personalized medicine. SERS has attracted considerable research attention in the fields of wearable flexible sensing and point-of-care testing (POCT) within medical diagnostics. Nonetheless, the integration of SERS with wearable technology presents several challenges, including device miniaturization, reliable biofluid sampling, user comfort, biocompatibility, and data interpretation. The ongoing advancements in nanotechnology and artificial intelligence are instrumental in addressing these challenges. This review provides a comprehensive analysis of design strategies for wearable SERS sensors and explores their applications within this domain. Finally, it addresses the current challenges in this area and the future prospects of combining SERS wearable sensors with other portable health monitoring systems for POCT medical diagnostics. Wearable SERS is a promising innovation in future healthcare, potentially enhancing individual health outcomes and reducing healthcare costs by fostering preventive health management approaches.