Comfortable urban outdoors are increasingly becoming difficult in the rapidly urbanizing tropics. While global climate change partly explains this reality, haphazard urbanisation is the primary cause for street level discomfort in the equatorial tropics. The study of the problem, exemplified by the urban heat island effect, is relatively new in the region, leading to a paucity of urban design and planning exemplars to tackle the negative consequences. Based on fifteen years of research on the urban climate anomaly in the warm-humid areas of Sri Lanka, this paper presents key challenges to outdoor comfort in the equatorial tropics and posits a way forward to a new approach to equatorial urban thermal comfort. Data and equity dimensions are explored.