Stetson started in 1865 when John B. Stetson — fresh off a failed gold prospecting trip out West — set up shop in Philadelphia. And though he didn’t strike it rich on the frontier, his trip did prove important in one regard: It led to the creation of Stetson’s original “Boss of the Plains” hat, the shape that helped Stetson become the largest hatting factory in the world by the early 20th Century. By the 1920s, Stetson was wildly popular with everyone from cowboys to Senators and Presidents, and despite the downturn in the popularity of hats by mid-century, the company soldiered on. In 2005, Stetson introduced a line of men’s and women’s footwear and apparel, and now, with a collaboration with award-winning Billy Reid under its belt, Stetson sits comfortably an undisputed icon of American style.