Despite our understanding that the microvasculature plays a multifaceted role in the development and progression of various conditions, we know little about the extent of this involvement. A need exists for non-invasive, clinically meaningful imaging modalities capable of elucidating microvascular information to aid in our understanding of disease, and to aid in the diagnosis/monitoring of disease for more patient-specific care. In this review article, a number of imaging techniques are summarized that have been utilized to investigate the microvasculature of skin, along with their advantages, disadvantages and future perspectives in preclinical and clinical settings. These techniques include dermoscopy, capillaroscopy, Doppler sonography, laser Doppler flowmetry (LDF) and perfusion imaging, laser speckle contrast imaging (LSCI), optical coherence tomography (OCT), including its Doppler and dynamic variant and the more recently developed OCT angiography (OCTA), photoacoustic imaging, and spatial frequency domain imaging (SFDI). Attention is largely, but not exclusively, placed on optical imaging modalities that use intrinsic optical signals to contrast the microvasculature. We conclude that whilst each imaging modality has been successful in filling a particular niche, there is no one, all-encompassing modality without inherent flaws. Therefore, the future of cutaneous microvascular imaging may lie in utilizing a multi-modal approach that will counter the disadvantages of individual systems to synergistically augment our imaging capabilities.