The cornerstone for any weather-ready wardrobe is a waterproof, breathable jacket. Opt for a more versatile shell jacket rather than a fully insulated jacket so you have the option to layer depending on the seasons and conditions. When shopping for a shell, find a fitted silhouette that is streamlined as a shell should not be bulky. Next, focus on details like fully taped seams, waterproof zippers, and laminated materials, preferably GORE-TEX. Not only are these details necessary to keep you dry, they’re also on trend. Brands like Nike Sportswear are integrating tech details like watertight zippers usually only seen in performance pieces into casual items like varsity jackets. A minimalist shell in a solid bright color with tonal details, like Beta FL by Arc’Teryx, works well with waxed denim or camo pants and woven sneakers for an urban, utilitarian outfit. A good shell packs up easily for trips and will last years if you look after it properly.

Style-wise, it’s besides the point to look dope. We’re talking life or death here and having wet, cold feet is a one-way ticket to pneumonia. Luckily there are many options for men’s boots. When it comes down to affordability, I almost always opt for Timberland, as I find nothing puts up with abuse better than a pair of classic 6-inch wheat Timbs. However, if you’re off Timbs, try an updated hiking silhouette. Diemme, an Italian shoe company, has a reputation for handmade footwear that is both hardy and beautiful. Their Roccia Vet boot is a sophisticated take on the traditional hiking boot and includes a Vibram sole for durability and stability and a leather and latex interior with guested tongue to ensure your feet stay warm and dry. Diemme also offers the Vibram sole in bright neon colors mixed with neutral uppers - think of them a more practical version of the Cole Haan Lunargrands. If Diemme is beyond your budget, try Native Shoes. Their hiking boot called the Fitzsimmons is similar in silhouette to the Diemme pair but retails at a reasonable $99.99 and come in a variety of both bright and neutral colors. The Fitzsimmons uses no animal materials and it’s even washable and odor resistant. When wearing any of the above boots, remember to opt for a sock using natural fibers like wool or cashmere and avoid regular cotton gym socks as they will not wick sweat leaving you with moist toes. Timbs, Diemmes and Natives all look just as good with denim or chinos and a varsity jacket as they do out in the wilderness so you can stay dry, warm and stylish while you’re in the streets. 

As a bonus tip, get a bottle of DWR (durable waterproofing repellent). You can wash and launder waterproof fabrics like GORE-TEX but the fabric may lose some water pilling ability over time. If you notice the raindrops are absorbing on your jacket or your boots instead of staying in droplets - it's time for a spray of DWR.