The utilization in architecture of computational design and digital fabrication, coupled with the exploration of new material systems, brings the potential to break with conventional ways of building. However, these emerging nonstandard structures also demand new ways of designing and proving the structure’s integrity and safety. This paper aims to develop an integrative structural design methodology and workflow to design, optimize, and validate nonstandard building systems by combining a multiscale and digital-physical approach. The methods are showcased with coreless filament winding (CFW) structures, an additive manufacturing method representative of nonstandard building systems made possible by robotic fabrication. The results demonstrate the potential of this methodology to shorten the gap between research and industry, facilitating the realization of innovative structures.