Urban forests notoriously lack diversity in the biological communities that inhabit them, from the age and species composition of street trees to wildlife populations. In reaction to invasions of nonnative insects and diseases as well as predicted response to climate change, an emerging number of community foresters and tree wardens are expanding their urban tree planting practices to include a broader assemblage of tree species. These include oaks, among other species able to tolerate and adapt to urban conditions. Oaks are potentially favorable in regions like the northeastern U.S., where they grow extensively in rural forests and demonstrate potential resistance to specific urban pests that have caused challenges for other historically popular and extensively planted street trees. Additionally, they are known to feature a number of wildlife benefits, and their ranges in the Northeast are predicted to expand under many future climate change forecast models. We examine the role of oaks in the urban environment through the lens of the urban forest diversity deficit, reviewing topics that include diversity recommendations, threats by nonnative insects and diseases, and the human-wildlife interface. The goal of this work is to encourage careful consideration of where and when to plant oak trees to help professionals address issues of uniformity, while achieving benefits for urban forest ecosystems and residents.