Urbanization can result in novel selective pressures that can cause phenotypic differences amongst urban-tolerant species across urban and non-urban habitats. Here, we compared the size of the white tail patch (“tail white”), a sexual signaling trait, in two urban populations of dark-eyed juncos in comparison to neighboring non-urban populations. Contrary to our expectations, urban phenotypes did not differ from local wildlands in San Diego and Los Angeles counties in similar directions. While the San Diego population showed lower tail white compared to its neighboring wildland population, the Los Angeles population did not. The tail white of the Los Angeles population was not statistically different from that of the San Diego population, suggesting that urban populations may share similar environmental conditions yet face different selective clines due to urbanization. There were, however, differences between wildland populations. Differences in evolutionary histories, environmental conditions, and selective pressures within and outside urban areas may affect how urbanization facilitates population differentiation, even across urban populations of the same species.