For over two decades, vascular stents have been widely used to treat clogged vessels, serving as a scaffold to enlarge the narrowed lumen and recover the arterial flow area. High-purity oligocrystalline austenitic steel is usually applied for the production of stents. Despite the popularity and benefit of stenting, it still may cause serious clinical adverse issues, such as in-stent restenosis and stent fracture. Therefore, the study of the mechanical properties of stents and in particular the prediction of their life cycles are in the focus of materials research. In our contribution, within the finite element method, a two-scale model of crack initiation in the microstructure of stents is elaborated. The approach is developed on the basis of the physically based Tanaka-Mura model (TMM), considering the evolution of shear bands during the crack initiation phase. The model allows for the analysis of the microstructure with respect to the life cycles of real materials. The effects of different loading conditions, grain orientation, and thickness of the specimen on Wöhler curves were analysed. It was found that the microstructural features of oligocrystals are very sensitive to different loading conditions with respect to their fatigue behaviour and play a major role in fatigue crack initiation. Different grain-orientation distributions result in qualitative and quantitative differences in stress distribution and in the number of cycles for crack initiation. It was found that presence of a neutral zone in the cut-out of the microstructure under three-point-bending loading conditions changes the qualitative and quantitative patterns of stress distribution and affects the number of cycles for crack initiation. It was found that under both tensile and bending loading conditions, thicker specimens require more cycles for crack initiation. The Wöhler curves for crack initiation in oligocrystalline microstructures of stents could be compared with the ones in the experiment, taking into account that for high cyclic fatigue (HCF), typically, more than 70% of the cycles refer to crack initiation. The developed numerical tools could be used for the material design of stents.