The company began making fabric for the wives of hunters, loggers and trappers, later outfitting the Civil War and Richard E. Byrd's 1939–1940 Antarctic expedition. Its mill at Chatham's Run grew into a company town that still bears the name Woolrich, and for generations the Rich family ran the business; the original 1830 mill is on the National Register of Historic Places.
After decades of competition from L.L.Bean, Eddie Bauer and Patagonia, the brand consolidated its European and U.S. operations under Italian company W.P. Lavori in 2016, with Japan's Goldwin also taking a stake. In 2023 it named Todd Snyder creative director of its Black Label collection, and in 2025 it showed its Fall menswear at Milan Fashion Week.