Style Scenario: Rugged, Stylish, Investment Worthy Everything

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What are you going to wear? Sometimes it’s good to look at a few suggestions then add your own tweaks and ideas. That’s what these are for. Winter should be no excuse to keep you from enjoying the outdoors, and doing so in style. Some days call for a full utilitarian outfit for trekking in the snow and other wintry mix, but on the days that are simply cold and call for light outdoor chores or socializing, strive to wear something that is both function AND form. Feeling good about how you look provides a mental confidence that is quite welcomed when the temperature goes down and you might wonder, “why am I out here?” You’re out here because it’s beautiful, and you’re beautiful, too.

Style Scenario: Dappered Lumberjack

The Jacket: Made in the USA Flint & Tinder Waxed Canvas Trucker in Coal – $268. One of if not the most popular thing Huckberry sells, and for good reason. The flannel-lined version of this jacket offers excellent warmth-to-weight ratio for moving about outdoors, while the waxed canvas provides a tough, durable exterior that looks and wears better the longer you own it. A bit stiff for a few weeks, but the more you ask of this jacket the better it feels. Full review can be found here. It quickly became my go-to jacket for temperatures above freezing. The Cheaper Option: Sticking with F&T here, and their on sale quilted waxed jacket. Not made in the USA though. Also, KUHL makes a waxed trucker in a similar “Ore” shade. That one goes for $159.

The Hat: Filson Watch Cap in Black- $45. 100% USA sourced wool to keep your noggin warm, from a stylish outdoor brand known for durable, hard wearing goods. The Cheaper Option: Huckberry. Those are hard to beat.

The Watch: Hamilton Khaki Field King Automatic – $575. Absolutes are overused, but I have no hesitation in saying this is THE pre-eminent style-forward outdoor watch. An incredible bang-for-your buck when you consider the mechanical specs well-suited to weekends in the woods: the day/date complication, 80 hour power reserve (!!!), sapphire crystal and stainless steel case. A legend, for good reason. Likely cheaper at a grey market dealer, but for nice automatic watches, I advocate for paying a bit of a premium (is MSRP really a premium, though?) for the peace of mind offered by a manufacturer warranty. The Cheaper Option: Many among us have owned, and loved, a Timex Expedition at one point or another.

The Shirt: L.L. Bean “Slightly Fitted” Scotch Plaid Flannel in Rob Roy Tartan – $50. It’s basically a lumberjack style scenario, so a traditional patterned flannel was to be expected. But this is honestly a cut above your average flannel shirt. Soft, cozy warmth in a slimmer-than-average flannel shirt from an heritage outdoor brand. L.L. Bean calls this “Rob Roy Tartan,” but it’s more commonly known as “Buffalo Plaid.” The fit is ideal for moving around outdoors – you don’t want it to be tailored or super slim-fitting. You also don’t want to look like a canvas bag. This fit from L.L. Bean strikes a perfect balance, and does so in a picture-perfect plaid pattern at a very affordable price. Hard-working and wearing, the shirt looks great with an added dash of thoughtfulness in the form of buttoned-down collars.

The Belt: Grant Stone Chromexcel Belt in Color #8 – $98. Another upgrade, and a worthy one at that. For most of us the majority of our belts are economy-minded, but a great item to treat yourself to is a high-quality leather belt. If you take care to occasionally condition the leather, this will last you many, many years. A stylish, but workwear-inspired belt made of thick – and I mean THICK – Horween Chromexcel leather holds up in the outdoors and looks dashing inside, too. The Cheaper Option: Going with this brown belt from gap. The brass-tone buckle is a nice touch.

The Boots: Grant Stone Cap Toe Boot in Forest Green Kudu – $340. Pricier than a typical boot for the outdoors, but Kudu leather is battle-tested in the wild. It isn’t winter leather, coming from the South African Greater Kudu antelope, but the the leather commonly shows scars from a life in the outdoors, making it suitably designed for this fancy lumberjack style scenario. The deep forest green is a dynamic shade of leather. Indoors, with overhead lighting, it can easily be mistaken for a black boot. But in natural outdoor light, the green pops through and shifts in hue and depth as the light catches it differently throughout the day and with each step. It’s a truly beautiful boot. For sizing reference, my pair in a 9.5D fit nearly identical (and even better) than my Allen Edmonds Higgins Mill Chromexcel boot in the same size. The Cheaper Option: Try these Waxy Nubuck Boots in Gray from Banana Republic. But wait for a sale. Should drop to $120 during a 40% off code.

The GlovesHestra Utsjo Leather Gloves – $115.50 ($165). Not cheap, but watch out for further codes and promos to drop these insulated just enough… dressy just enough… yet also just tough enough gloves from Hestra. The Cheaper Option: They aren’t very “Dappered” but the Duluth Trading Company Alaskan Lightweight Work Glove goes for fifty bucks, is waterproof and offers ample protection from the wind, and looks nicer than your average work-oriented glove.

The Socks: Darn Tough Mountaineering Sock in Grey- $30. Merino wool for breathability, but built for “subzero” temperatures on the mountain. It should do the trick for any normal outdoor task you throw at it. For something with a lower cut, this full-cushion hiking boot sock from Darn Tough works wonders. The Cheaper Option: Bombas does merino wool socks for $19, but they don’t have the hiking/outdoorsy heritage that Darn Tough has.

The Jeans: Banana Republic Watershed Mill Valley Jeans in Rinse Dark Wash – $95 ($119). Or whatever dark wash denim jean you happen to favor. Opting for jeans instead of cords here for harder-wearing winter activities is the smart choice, while staying more polished than a pair of full-fledged work pants. These “Watershed” denim pants from BR use recycled plastic bottles in the fabric blend. At 5% it’s a small portion, but in conjunction with 5% recycled cotton, every little bit helps move us to a more sustainable stylish future. The Cheaper Option: Nothing is more affordable (and sustainable) than wearing the pants/jeans you own. Most of us have plenty of jeans already. Wear what you have. Wear them to death, then when you’re ready for an upgrade, consider the pair from BR.

The Knife: Benchmade Griptilian – $136. I won’t bog you down with blade specifications and steel quality, handle material, or locking mechanisms. I’ll simply say – this is a great everyday carry knife for normal cutting or slicing tasks. This is my personal EDC knife, and after a year of regular use, it looks nearly brand new. This may seem like a steep price for “just a knife,” but when you’re in a pinch and NEED a knife, the quality matters, and price does reflect quality within this segment. For really hard tasks, opt for a fixed blade knife with upgraded steel, but a folder gets the nod here for ease of carry – and it’s cheaper, too.

For your lips: Jack Black SPF 25 Lip Balm – 2 for $12. Dry, cut-up, split, and/or peeling lips aren’t stylish. Protect yourself against the elements.

About the Author: Jason P. spends his days working in the creative marketing department of a big telecom company. He also does a bit of real estate investing on the side. He believes in curating a timeless, classic wardrobe with subtle modern touches for today. He and his wife love hiking with their dog and shopping at local small businesses and antique stores when they travel. Jason is a practitioner of muay thai and traditional boxing, and his favorite drink is a hoppy New England IPA.