Urban environments have become significantly brighter and more illuminated, and cities now consider media architecture and non-static, self-luminous LED displays an essential element of their strategy to attract residents, visitors, and tourists in the hours after dark. Unfortunately, most often, they are not designed with care, consideration, and awareness, nor do they support the visual wellbeing and circadian rhythms of humans. They also increase light pollution which has an adverse effect on the environment. The aim of this study was to estimate the scale of the negative impact of 28 non-static, self-luminous LED shop window displays within a real-life city context along the main shopping street Banhofstrasse in Zurich, Switzerland. An experimental field measurement survey investigation was performed to identify visual luminance with commonly available tools such as a luminance meter and a digital reflex camera for luminance photography. Moreover, the most important global approaches to reduce light pollution were evaluated in the form of existing guidelines, technical standards, and laws, all of which should be considered when specifying illuminated digital advertisements. A literature review and survey results both confirmed the extent of the problem and highlighted, too, the need to better measure, apply, and manage this new technology. The authors’ proposal for improvements involve practical recommendations for the design and implementation of future projects which can positively guide and direct this growing trend.