‘Tis still the season to … layer up with winter style essentials, is it not? And so we begin another #OOTD, taking on a tricky question that can spring up during the doldrums of winter: “Do I really have to wear that jacket again?” Maybe it’s the coat you always wear. Maybe it’s got you feeling like you need a change of pace. Fear not, my friends — I’m here to present the humbler trucker jacket as one of the best new pieces of outerwear you can layer up with. Particularly if it’s not snowing like crazy, and temperatures aren’t in the single digits, it pays to have a whole host of go-to winter style picks that are just different enough from the everyday — in this case, we’re talking about an American-made fleece trucker jacket that’ll keep you warm and toasty when paired with, say a classic long-sleeve shirt from Buck Mason and a rugged denim shirt. It’s a solid change of pace from the ordinary, and it can always be fun to switch things up. The rest of this look is as classic as can be, perfect for a laidback weekend outing, an afternoon at your favorite burger bar, a quick weekend getaway, and perhaps, just maybe … super-casual Friday at work. After all, we’ve got classic chinos and stylish leather boots in the mix, too. You’re going for a look that’s not too over-the-top, but one that just works when it comes to the right style essentials for the season. To get the full picture, keep scrolling, reading and shopping. Like what you see? Let me know all about it on Twitter.

All of the rugged gear picks you need to stay warm in style this winter.

• The Trucker Jacket: American Giant Fleece Trucker Jacket, $208 — The trucker jacket in question is different than you might expect — yes indeed, this rugged trucker jacket is made from fleece and features a zip front, all the better to layer this winter. Speaking of layering …
• The Stylish Long-Sleeve Tee: Buck Mason Sueded Cotton Long-Sleeve Tee, $48 — For prime winter layering, start things off with a classic long-sleeve shirt from Buck Mason that just so happens to be as easy to wear on its own as it is to layer with a rugged denim shirt. And on that note …
• The Denim Shirt: Buck Mason Vintage Denim One-Pocket Shirt, $105 — Folks, you need a rugged denim shirt in your wardrobe — preferably, one that’s polished and yet ever-so-slightly edgy, like this handsome number from Buck Mason.
• The Pants: Flint and Tinder 365 Pants, $98 — Not yet familiar with some of the best five-pocket pants around? Take care of that right now with these classic chinos from Flint and Tinder — an ideal pairing alongside a trucker and your rugged denim shirt. 
• The Rugged Leather Boots: HELM Boots Muller Teak Boots, $385 — The best pair of winter footwear in this case just so happens to be these stylish leather boots from HELM Boots. Durable, dependable & available for a steal — you can get $50 off your first pair of boots, plus free shipping.
• The Watch: Zodiac Watches Grandville Watch, $495 — The only way to close out this #OOTD? With a rugged, stylish leather watch on your wrist — the kind that looks great at home and at the office, no less.
• The Grooming Essential: Duke Cannon Trench Warfare Deodorant, $10 — Yes indeed, you shouldn’t be sleeping on your grooming essentials this winter. In this case, Duke Cannon has you covered with its Trench Warfare Deodorant, one of the best men’s deodorants you’re apt to try right now.
• The Everyday Carry Essential: Tanner Goods Simple Tote, $130 — Gear up for whatever’s out there with a surprisingly rugged tote bag from Tanner Goods, the perfect catch-all bag for everything from your laptop to the rest of your EDC.

OK, do you have a better idea of how to dress for winter — and how to wear a trucker jacket for winter? It’s something that at first glance might not make a ton of sense, but when done the right way (especially with a warm fleece trucker jacket from American Giant), it can provide plenty of benefits. The best layers for winter are really critical here, too — so, a classic long-sleeve shirt from Buck Mason is going to keep you nice and warm without being overly stuffy. The same goes for your classic denim shirt, also from Buck Mason — talk about a one-two punches that delivers perfectly casual-yet-versatile style potential. Things get amped up ever-so-slightly without going over the top via classic chinos from Flint and Tinder, which also offer up office-friendly (or brewery-ready) style when teamed up with stylish leather boots from HELM Boots — those boots in particularly will age wonderfully over time. They’ll also work in tandem with a rugged, stylish leather watch for a dash of adventure-minded functionality. And thankfully, one of the best men’s deodorants is going to keep you smelling and feeling great — just as a rugged tote bag from Tanner Goods is going to get your gear essentials from point A to point B in style. That’ll about wrap up this #OOTD — where is it going to take you this winter? Great places, I hope. Thanks for reading — cheers!