The fabrication of electrospun polymer fibers is demonstrated with anisotropic cross-sections by applying a simple pressing method. Electrospun polystyrene or poly(methyl methacrylate) fibers are pressed by flat or patterned substrates while the samples are annealed at elevated temperatures. The shapes and morphologies of the pressed polymer fibers are controlled by the experimental conditions such as the pressing force, the pressing temperature, the pressing time, and the surface pattern of the substrate. At the same pressing force, the shape changes of the polymer fibers can be controlled by the pressing time. For shorter pressing times, the deformation process is dominated by the effect of pressing and fibers with barrel-shaped cross-sections can be generated. For longer pressing times, the effect of wetting becomes more important and fibers with dumbbell-shaped cross-sections can be obtained. Hierarchical polymer fibers with nanorods are fabricated by pressing the fibers with porous anodic aluminum oxide templates.