To develop a waterproof breathable material, we fabricated three kinds of nanofiber web laminates using a massproduced electrospun nanofiber web with different substrates and layer structures. The waterproofness and breathability of nanofiber web laminates were evaluated after repeated launderings and compared with those of conventional waterproof breathable fabrics currently in use, including densely woven fabric, microporous membrane laminated fabric, and coated fabric. The durability of nanofiber web laminates, including adhesion strength, abrasion resistance, tensile strength, and tearing strength, was also assessed and compared with those of conventional waterproof breathable fabrics. The water vapor transmission of nanofiber web laminates increased slightly after repeated launderings, whereas the air permeability somewhat decreased after launderings but still maintained an acceptable level of air permeability. Laundering reduced the resistance to water penetration of nanofiber web laminates, which implies that laminating techniques or substrate materials that could support waterproofness of the laminated structure should be explored. The adhesion strength, abrasion resistance, tensile strength, and tearing strength of nanofiber web laminates were in a range comparable to conventional waterproof breathable materials.