Left: Whether you're lounging in front of a fire or shivering in a snow cave, whiskey tastes better when sipped out of Sigg's stainless-steel Vintage Flask ($28; mysigg.com). See the difference: Bushnell's rain- and fog-proof, 10x42 e2 allows 99.7 percent light transmission per lens ($500; bushnell.com). Steve McQueen made Persol's foldable 714 sunglasses famous in 1968's The Thomas Crown Affair. It's cooler than ever to be like Steve ($250; persol.com). The jackknife, all grown up: The limited-edition, rosewood-encased Victorinox Swiss Army SwissChamp LE Knife comes with everything from a wire stripper to a chisel ($145; swissarmy.com). Named after La Carrera Panamericana—the epic sports-car race across Mexico—the TAG Heuer Carrera Automatic Chronograph Tachymeter, with its classic face, is as elegant as the 1963 original ($2,895; tagheuer.com).
Right: Swiss Army's Cotton Military Styled Cargo Pant and Military Flannel Shirt are sharp enough for the office yet casual enough for cocktail hour ($175, $145; swissarmy.com). If you're going to get someone a sweater for Christmas, make it the decadently soft and athletically cut Cashmere Crew from Patagonia ($200; patagonia.com). Polo's versatile, 100 percent cashmere Balmorrow Glenplaid Scarf is the downtown equivalent of a balaclava ($224; ralphlauren.com). Sometimes the best style is sly: Hiding below the understated exterior of Modern Amusement's 100 percent cotton Williamsburg Parka is a whimsical liner patterned with brightly colored birds ($225; modernamusement.com). Handcrafted from the same type of leather Pony Express riders used for their saddlebags, Mulholland Brothers' medium Hippo Duffel is weekend-size but still meets carry-on rules ($795; mulhollandbrothers.com).