Australians have the highest incidence of melanoma globally, despite increasing awareness of the risks of excessive sun exposure. Although excess ultraviolet radiation (UVR) can cause irreparable cell damage and lead to cancer, some exposure is vital to maintain bodily processes such as vitamin D production. For an individual, finding the balance between healthy exposure and skin damage is largely guesswork. The ability to provide a simple, individualised indicator of cumulative UVR dosage could be transformative in preventing skin cancer. This review will provide a brief overview of the variety of UVR sensor technologies and explain the important role of colourimetric dosimeters. The chemistry behind some recent examples of colourimetric dosimeters will be discussed, identifying that molecular photoswitches are ideal candidates to enable this technology. We discuss the chemical mechanisms of photoswitches and how to modify their chemical structure to optimise their properties for use as dosimeters. Through this lens, diarylethenes have been identified as prime dosimeter candidates, owing to their sensitivity, stability, adaptability and the variety of visually striking colours possible. Finally, some specific challenges are identified in the design and fabrication of personalised colourimetric dosimeters that can equitably meet the requirements of all users in our community.