Introducing haute Americana, one of the most powerful—and paradoxical—forces in men's sportswear. Until recently, men like Leung would've skipped the Woolrich for a skinny Dior suit. But in recent years a number of tastemakers, many foreign, have dedicated themselves to reviving iconic American clothing for a hip new audience. Some have collaborated with classic U.S. brands on revitalized products (see: Suzuki and Woolrich). Some have stocked hunting garb in their big-city boutiques. And some have actually begun to reproduce emblematic gear—Wayfarers, Penfield vests—to exacting standards of authenticity. The result—on ample display in places like Brooklyn, N.Y., and Portland, Ore., where certain streets now resemble catwalks crowded with bookish lumberjacks—is a subset of prosperous peacocks paying a premium for garments originally meant for mining or fishing, then wearing them to tapas bars and...