With demographic change becoming an ever more pressing issue in Germany, old age (80+) is currently talked about above all in terms of being a problem. In mainstream discourse on the situation of the oldest old an interpretive framework has emerged that effectively rules out the possibility of people living positively and well in old age. With regard to both individual (personal) and collective (societal) spheres, negative images of old age dominate public debate. This is the starting point for an interdisciplinary research project designed to look at the ways in which people manage to "live well in old age in the face of vulnerability and finitude"--in express contrast to dominant negative perspectives. Based on the results of this project, the present article addresses an attitudinal and behavioral mode which we have coined "senior coolness". Coolness here is understood as both a socio-cultural resource and an individualized habitus of everyday living. By providing an effective strategy of self-assertion, this ability can, as we show, be just as important for elderly people as for anyone else. "Senior coolness" is discussed, finally, as a phenomenon that testifies to the ways elderly people retain a positive outlook on life--especially in the face of difficult circumstances and powerful socio-cultural pressures.