The wilderness might be more unforgiving in its perils, but never underestimate the challenges of the City: fording slush-puddled sidewalks. Spelunking fetid J-Train stations. Gristedes. Outfit your urban wanderlust with Napapijri's Sidewalk Collection.
An Italian company that inexplicably flies Norway's flag, NJ carved their rep with technical gear inspired equally by arctic adventurers and Euro fashion -- like Sir Edmund Hillary would've sported at "Disco Everest (sherpas free before 10pm!)". But Sidewalk's sturdily natty button-downs, sweaters, pullovers, and outerwear are optimized for explorers more comfortable with hoofing pavement than drinking their own urine for survival. Vestiges of their rugged origins include jackets lined with perforated cotton (to regulate temperature by circulating air), shirts with jersey-lined cuffs (to prevent frostbite, or just chillybite), and jackets sporting rip-stop nylon -- which stands up to even the pointiest anti-bum-nap spikes.
NJ also offers a free travel journal with any piece of Sidewalk clothing, perfect for recording travails, e.g., "Dear Diary, entire party fell into The Gap, repairing to base camp for Greek tapas and dermabrasion."