#OOTD: Step Out in Classic Winter Style This Season With Your New Favorite Gear

So, my friends — here we are. The last day of 2019 — can you believe it?? Make no mistake, you can still roll your favorite style essentials (like this #OOTD) into 2020. In fact, I highly recommend it. Now, as I’m sure you know, it’s New Year’s Eve. Presumably, you’re prepared for the big night? But we’re going to look ahead a little bit, with the sort of winter style essentials you can wear beyond just tonight (although if you still need some help with what to wear on New Year’s Eve, you should check out that post as linked there). We’re talking about gear that’s fit for a casual office or a weekend happy hour in equal measure. Heck, if your New Year’s Eve is going to be more casual, then this should provide some inspiration, too. That being said, you’ll recognize the right men’s style gear for winter regardless, from a classic crewneck sweater to your new favorite flannel shirt and beyond. Again, the emphasis is on gear that you can wear beyond just a fancy New Year’s Eve, and I think you’ll be mighty pleased at the versatility we’re giving you to start 2020. Yes, that includes rugged leather boots and a tough casual watch, as well as plenty of new everyday favorites. So, how about it? Let’s show you how to start 2020 the right way. Like what you see? Head to my Instagram for more real-time men’s style tips. 

Taking the classics you know and love, then amping them up just a bit for winter.

  • The Classic Sweatshirt: Birdwell Beach Britches Garment-Dyed Raglan Crew, $89.95 — The folks at Birdwell Beach Britches have been making classically rugged-yet-laidback gear for decades now, from swim trunks to essential winter style picks like this classic crewneck sweatshirt in a handsome shade of indigo. The perfect winter sweater (I should know, I’ve been testing it courtesy of the brand!).
  • The Shirt: Western Rise TechWool Flannel Shirt, $119 — A classic crewneck sweatshirt like the onne seen above can be layered up with just about anything — especially this stylish flannel shirt from Western Rise. It’s moisture-wicking to keep you comfortable, and this is also a uniquely office-ready flannel shirt.
  • The Jacket: Flint and Tinder Golden Bear Leather Jacket, $998 — Now, is this classic leather jacket well-suited for, say, the polar vortex? Not quite — but the rest of the time? Yes indeed, this is one of the best leather jackets your menswear writer has seen in some time. In fact, one could say every guy needs a leather bomber jacket in his rotation, and this is the one to buy.
  • The Pants: Duluth Trading Co. DuluthFlex Ballroom Slim-Fit Khaki Pants, $59.50 — This is a classic pairing all the way through — slim, surprisingly durable chinos and one of the best leather jackets never fails. These Duluth Trading Co. khakis are made from pre-washed cotton twill and spandex for comfort and durability; they’ll also provide great mobility thanks to the Hidden Crouch Gusset®.
  • The Boots: HELM Boots Marion Color No. 8 Boots, $395 — For rugged style that’s fit for winter weather and the office, you need some of the best men’s boots — like these absurdly beautiful HELM boots made with color No. 8 Horween chromexcel leather.
  • The Watch: Martenero Kerrison Watch, $595 –The only way to round out this outfit is with a tough casual watch. In fact, Martenero has quite the habit of making some of the best leather watches on the market. This is the one you need.
  • The Grooming Essential: Duke Cannon Solid Cologne, $25 — Yes, you need some Duke Cannon Solid Cologne in your life. Some of the best men’s solid cologne can give you as much confidence and style as, say, one of the
  • The Everyday Bag: Filson Ballistic Nylon Duffel Backpack, $245 — Whatever your day calls for, be it punching the clock at work or heading across town to grab a coffee, your everyday carry essentials need this tough Filson bag.

The fun thing about taking stock of the men’s style essentials you’ve got in your wardrobe — or perhaps, the ones you need to add — really starts when you realize the versatility you’ve got at your fingertips. How so, Beau? Well, this outfit has a bit of everything, including a classic crewneck sweatshirt that gets a dressier update thanks to the way you layer it up with a stylish flannel shirt. That makes this combo both office and weekend-ready, and it only gets better — it’s helped along by surprisingly tough Duluth Trading Co. chinos that work from Monday through Sunday. The real unsung hero might be that classic leather jacket from Flint and Tinder — seriously, can you ever go wrong with one of the best leather jackets, especially when it’s warm, cozy and durable? Of course, no outfit in cold winter weather is complete without some of the best men’s boots, particularly when they’re made with remarkable color No. 8 Horween chromexcel leather. See, we’re bringing together plenty of what you already have, including a tough Filson bag and naturally, one of the best leather watches you can throw on your wrist. Wrap it all up with Duke Cannon Solid Cologne, then be prepared for the compliments to head your way … non-stop.

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