Ready to layer up for winter? In particular, ready to wear your new favorite cardigan to power through the rest of the season? We’re kicking things off with an extremely luxurious, investment-level cardigan from my friends at Buck Mason — if you follow me on Instagram, you’ve surely seen how I’ve been wearing it. And now, we’re telling you how to wear it for the weeks and months ahead. It’s an extremely easy cardigan to layer, particularly when you pair it with a stylish flannel shirt from Flint and Tinder, along with an equally classic henley from that same brand. Slim denim from Bluffworks — launched earlier this year — keeps this #OOTD crisp and casual. Rugged leather boots give you the option to stomp through the snow on the weekend, or head to the office on a casual Friday (more on that in a second). And again, it all comes back to this stylish, rugged cardigan — this is the type of piece that a style icon like Steve McQueen might have worn, and it’s ably complemented by a classic casual watch and other winter-ready favorites. The only question is, where the heck are you going to wear it? It’s simple, trust me. So, without further ado … here we go.

A classic, premium cardigan, accented by a rugged flannel shirt & tough leather boots. Hello, winter.
- The Cardigan: Buck Mason Vintage Cashmere Shawl Cardigan, $225 — We’ve previously covered this classic cardigan on the blog, and it’s very much worth another look. Premium, rugged, utterly classic.
- The Classic Flannel Shirt: Flint and Tinder Flannel Button Down, $118 — Leave it to Flint and Tinder to again make your new favorite flannel shirt. Perfect for winter.
- The Henley: Flint and Tinder Heavyweight Henley, $62 — Lest we forget, this American-made brand also makes a heck of a stylish henley.
- The Denim: Bluffworks Departure Travel Jeans, $125 — Denim that moves with you — not against — is a must when navigating snowy winter streets, and Bluffwork gets it right with the launch of these new, travel-friendly jeans.
- The Rugged Boots: White’s Boots MP-M1 Boots, $600 — It’s going to be really tough to top these simply incredible, highly stylish leather boots — a truly great offering from White’s Boots.
- The Watch: Zodiac Grandville Watch, $495 — This outfit calls for a rugged casual watch, without a doubt. The Zodiac Grandville Watch steps up to the plate nicely.
- The Socks: CHUP Hazelwood Socks, $35 — I’m of the opinion — as you all know — that stylish socks are a go-to in any situation, and CHUP assuredly makes some of the best men’s socks out there.
- The Stylish Winter Hat: Faherty Brand Peak Cap, $98 — It’s cold and snowy out there, so this warm winter cap from Faherty Brand is essential.
- The Men’s Grooming Essentials: Wise Essentials Bundle, $64.98 — When tough winter weather hits, you need to keep your face and skin in check; fortunately, these are some of the best men’s winter grooming picks to help you along.
- The Everyday Carry Essential: Hitch and Timber EDC Slip, $115 — The little details really add up, and the Hitch and Timber EDC Slip is crucial & well-designed.
Now, the thing about wearing a classic, rugged cardigan like this one from Buck Mason is that it gives you the ultimate in versatility. Use it as a top layer with a scarf for a Sunday park stroll on a warmer-than-expected winter day, or wear it to the office in place of a blazer — the rest of the pieces in this #OOTD can help you there, too. That process starts with a stylish flannel shirt from the great men’s style purveyors at Flint and Tinder, and carries through to the slim, comfortable denim on tap from Bluffworks. You can choose to keep the stylish henley as part of this outfit (for a casual weekend brewery outing) or you can lose the henley and perhaps throw on a textured slim wool tie if you need to class things up for the office. Step into a durable pair of leather boots — I.E. The outstanding White’s Boots shown above — and then round out your ensemble with stylish patterned socks and a warm winter cap from Faherty Brand. It’s a can’t-miss combo that only gets better when you wear the Zodiac Grandville Watch.Keep your mug looking fresh with some of the best men’s winter grooming picks, and then be sure to reach for the handy, essential Hitch and Timber EDC Slip — all of that, to me, sounds like the makings of a new favorite winter outfit. To keep up with how I’m getting dressed for winter, be sure to follow me on Instagram. Thanks for reading!
-Beau