Variable-angle filament-wound (VAFW) cylinders are herein optimized for minimum mass under manufacturing constraints, and for various design loads. A design parameterization based on a second-order polynomial variation of the tow winding angle along the axial direction of the cylinders is utilized to explore the nonlinear steering-thickness dependency in VAFW structures, whereby the thickness becomes a function of the filament steering angle. Particle swarm optimization coupled with three Kriging-based metamodels is used to find the optimum designs. A single-curvature Bogner–Fox–Schmit–Castro finite element is formulated to accurately and efficiently represent the variable stiffness properties of the shells, and verifications are performed using a general purpose plate element. Alongside the main optimization studies, a vast analysis of the design space is performed using the metamodels, showing a gap in the design space for the buckling strength that is confirmed by genetic algorithm optimizations. Extreme lightweight while buckling-resistant designs are reached, along with non-conventional optimum layouts thanks to the high degree of thickness build-up tailoring.