This article extends Qviström's (2007; Geografiska Annaler: Series B, Human Geography 89 (3): 269-282) ideas concerning "landscapes out of order" within a re-discovering and re-imagining of spatial planning theory and practice. Taking the viewpoint that planners and decision-makers order and manage space in prescribed and constrained ways, the article argues that this can hinder innovative practices which have the potential to deliver significant societal and environmental benefits. Using case studies from permaculture and guerrilla gardening, we illustrate how planning practice can be rooted in confrontation and legal challenge rather than with more positive and inclusive approaches, as is envisaged within spatial planning theory. Clearly, the ways in which such initiatives intersect with the planning system raise important questions about joined-up policy across scales and sectors, and the ability of planning to be a proactive vehicle of environmental and social change. Our findings confirm that spatial planning theory is largely "disintegrated" (Scott et al. 2013; Progress in Planning 83: 1-52) from much contemporary planning and environmental practice and wider discourses of sustainability. This suggests an urgent re-examination of the spirit and purpose of planning to embrace and promote the new even where they challenge established orthodoxy and planning order.