Stylish, clued-up men are looking beyond Patagonia and going gaga for a new wave of hiking-style clothes. They’re good-looking—and, often, pricey. Call it Gorpcore 2.0.

No matter how classic or avant-garde your style is, you probably have one or two combinations you default to when you don’t know what to wear. Through this series, I’m giving you tips to refresh some ...