Seph Skerritt, who had no fashion background, no investors and no industry connections, founded Proper Cloth in New York in 2008 around a simple idea: make custom-fit dress shirts easy to buy online. By his own account the first two years were humble ones before the business found its footing. It later opened its first physical showroom in SoHo in 2013, followed by a Fifth Avenue location in 2019 and further showrooms in Washington D.C. and Chicago, expanding from shirts into suits and sport coats along the way.