Cities are rapidly transforming into complex places which traditional approaches to urban planning have difficulties to deal with. The new EU- and UN-urban agendas still lack gender-awareness concerning the supportive infrastructure of everyday life that enhances the opportunities for both women and men with different backgrounds and orientations to muddle through in the complex daily contexts. I argue that, in addition to mainstreaming gender equality as a top-down endeavour, there is a need for an expansion of engendering urban planning, which requires different ways of dealing with varying types of planning from the gender perspective. The aim of the article is to present and discuss the results of an explorative study with qualitative methods which has tested with examples a framework for engendering urban planning in different contexts. These are (1) Gender mainstreaming comprehensive urban planning (Vienna); (2) Gender-sensitive advocacy planning (Barcelona); (3) Gender+ self-organizing around urban planning & development (Helsinki); (4) Gender-aware co-governance with public, private, people-partnerships (Athens). The results corroborate the argument but lead to a new one concerning the engendering of new approaches, such as Expanded urban planning that might alleviate dealing with complexities.