Measurements of the thermal properties of the skin can serve as the basis for a noninvasive, quantitative characterization of dermatological health and physiological status. Applications range from the detection of subtle spatiotemporal changes in skin temperature associated with thermoregulatory processes, to the evaluation of depth-dependent compositional properties and hydration levels, to the assessment of various features of microvascular/macrovascular blood flow. Examples of recent advances for performing such measurements include thin, skin-interfaced systems that enable continuous, real-time monitoring of the intrinsic thermal properties of the skin beyond its superficial layers, with a path to reliable, inexpensive instruments that offer potential for widespread use as diagnostic tools in clinical settings or in the home. This paper reviews the foundational aspects of the latest thermal sensing techniques with applicability to the skin, summarizes the various devices that exploit these concepts, and provides an overview of specific areas of application in the context of skin health. A concluding section presents an outlook on the challenges and prospects for research in this field.