For more than a decade scholars mostly from economy and development studies have described the rise of a newly emerging ‘middle class’ in the Global South including Africa. This has led to a ‘middle class narrative’ with the ‘middle class’ as the backbone of economic and democratic development. Especially with regard to the stability of the position of the people in the ‘middle’, empirical social science studies challenge the ‘middle class narrative’ and at their uncertainty and insecurity. This tension between upward mobility at the one hand uncertainty and instability at the other hand (the vulnerability-security nexus) and the options to cope with this challenge under the condition of limited provision of formal social security is the focus of this case study on Kenya. Instead of an analysis of inequality based on income, it is more helpful to start from the welfare mix and the role of social networks as main elements of provision of social security. Against this background, we identify different strategies of coping that go together with different sets of values and lifestyles, conceptualised as milieus, that are not determined by the socio-economic situation.