The degree of lip dryness is accompanied by the changes in atmospheric temperature and/or humidity. In an attempt to relieve lip dryness, lip is commonly and involuntarily licked. When lip dryness becomes noticeable, people often apply products such as lip balm to protect the lips, but this may be insufficient to hydrate them because toothpaste and facial wash tend to dry them whenever they are used. Also, during the dry winter season, involuntary lip-licking to hydrate the lips becomes habitual, even among adults, occasionally leading to lip-licking dermatitis. Apart from lip-licking, tooth brushing and lip-biking are able to make lips more prone to get dry and sore. The overall evaluation on lip appearance is often reflected by the severity of chapped lips (e.g., cracks and/or peels), but due to the variation in individual’s sensitivities, the subjective dryness assessment does not necessarily agree with the objective evaluation. Therefore, we tried to develop an objective lip dryness scoring system based on the analysis of UV light-exposed lip images that could capture the dryness conditions usually undetectable through medical interviews or gross examination. We also discussed how subjective and objective lip evaluations were associated with daily life-related matters derived from medical interviews and questionnaires.