Intensification and specialisation of agriculture and forest use has led to profound structural and compositional changes in European landscapes. In particular, sharp, narrow edges adjacent to relatively homogenous vegetation types progressively replace transitional habitats, crucial for a plethora of species and ecological processes. Quercus robur and Q. petraea regeneration niches make them best adapted to such transitional habitats. However, contemporary oaks’ importance, including their regeneration, is usually considered within limits of forest habitats. Defining habitats, landscape patterns and processes fostering oak regeneration and ‘oakscape’ development. We assessed the state-of-the art of the topical literature with respect to various aspects of oak regeneration based on a refined list of 234 titles from the Web of Science database. The review confirmed that the vast majority of studies focus on forest habitats, disregarding the fact that substantial part of acorns are being carried away and seeded by birds in non-forest habitats. The common acceptance of the simplistic landscape mosaic model, based on segregated homogenous vegetation categories and clear-cut lines separating patches, impedes proper assessment of landscape changes, referring to ‘untypical’, transitional habitats—the true oaks’ domain. Hence, restoring and sustaining European ‘oakscape’ should result from the overall landscape management, based on a better adapted gradient approach to landscape studies. Applying such an approach, we identified a set of habitats fostering successful oak regeneration and recruitment without direct human support, contributing to the contemporary ‘oakscape’, represented mostly by non-forest, either natural or anthropogenic habitats.