If you keep up with the digital pages of your favorite menswear blog (this one!), then you know that we positively love recommending a stylish henley for many a situation — and this crucial piece of menswear is perhaps no more important than during the winter months. The right henley to buy now can in fact be used as a crucial base layer — particularly the stylish indigo henley from Faherty Brand that forms the foundation of this #OOTD. It’s the perfect piece to complement the other gear picks on display here — taken in total, this is a rugged, causal, warm ensemble that I could see working everywhere from a laidback weekend bar outing to a snowy winter hike. Again, it all starts with a great henley, that classic men’s style staple that started as a sporting shirt and has now evolved into the shirt that every guy needs (arguably). So, why does this entire outfit stand on its own? You’ll see why in just a second, but know that we’re teaming up our rugged henley with a classic flannel shirt, durable work pants and a pair of the best men’s boots for winter. It’s all topped off with — naturally — a seriously warm sherpa trucker jacket from Flint and Tinder. Now, let’s unveil the ensemble, shall we? To see how I’m styling a henley this winter, head to my Instagram.

• The Jacket: Flint and Tinder Type 3 Sherpa-Lined Jacket, $208 — An incredibly cozy, perfectly rugged sherpa jacket to keep you warm in style. Flint and Tinder is just the right way to start off this ensemble.
• The Classic Henley: Faherty Brand Long-Sleeve Indigo Henley, $98 — Here’s the stylish henley in question — the fabric used for this Faherty Brand henley should be exceptional & perfect for layering.
• The Shirt: California Cowboy High Sierra Shirt, $148 — Speaking of layering, this stylish flannel shirt is just what the doctor ordered atop a rugged henley.
• The Boots: Thorogood Beloit Boots, $300 — Looking for some of the best men’s boots for winter? Of course you are. These are simple yet subtly stylish.
• The Pants: Iron & Resin Union Work Pants, $155 — Make no mistake, these rugged work pants are the right way to combat winter’s worst weather. Iron & Resin gets it right.
• The Watch: BOLDR Supply Co. Venture Watch, $137 —  Your search for the perfect casual watch ends here, thanks to BOLDR Supply Co. 
• The Socks: American Trench Merino Activity Socks, $19 — A pair of the best men’s boots for winter calls for a pair of the best men’s socks that your money can buy. These American Trench socks fit the bill.
• The Winter Hat: Iron & Resin Watchman Beanie, $28 — Last but not least, a stylish beanie cap is the ideal way to top off this #OOTD. That’s all there is to it.

OK, folks — what do we think of the choices for this rugged, casual, exceptionally timeless winter look? To me, the base layer of a stylish henley is what makes it all go — especially one from Faherty Brand, guaranteed to be comfortable and easy to layer. That’s all the better when you consider the stylish flannel shirt we’re wearing atop it, right? And things only get warmer and better-looking from there: The Flint and Tinder Type 3 Sherpa-Lined Jacket really is as good as it gets. It’s the type of jacket that could take you on a brewery tour or through a museum trip, then out to a casual gastropub — the same can be said of the surprisingly versatile Union Work Pants from Iron & Resin.  The entire combo is elevated even further thanks to the tremendous Thorogood Beloit Boots (easily the best leather boots for the season). And your accessories will add some sheen to this outfit if you focus on picking up arguably the perfect casual watch — one that’s going to stand up to the challenge of winter weather and go-anywhere style. You could certainly say the same thing about your American Trench socks, which add another element of comfort and all-day performance. Again, trekking from a gallery to a brewery to drinks has never been so easy. Last but certainly not least, it really will pay off to put on a stylish beanie cap as temperatures continue to drop. Now, with all of that being said … where will this outfit take you? Let me know via The Style Guide Facebook page.