OK, so today’s #OOTD is going to tackle familiar territory for anyonoe who reads the blog regularly — we’re talking about one of the best men’s henleys, and specifically, how to wear a henley for winter. Is this the sort of topic that gets covered a lot on ye olde Style Guide? It sure is — but does that make it any less useful for the doldrums of winter? Absolutely not. You can always use more ways to wear a henley (or a refresher course, at that). The henley in question is the excellent Flint and Tinder Organic Slub Cotton Henley, a durable henley that won’t weigh you down — the sort you can layer with (as you’ll see) a classic flannel shirt and a durable waxed parka.  Together, these gear picks keep you toasty and sharp no matter where you’re headed, particularly if you’ve got to take on the snow during a winter weekend getaway — or on your commute, or during a daring weekend brunch run. While a rugged henley won’t cut it for scenarios where a blazer is the norm, I’m accustomed to wearing something similar to my office most days — maybe that type of look works for you, too? Regardless, you need all the layers you can get during the depths of winter (not to mention rugged leather boots, which you’ll also find below). When you feel a chill in the air, best to layer up with one of the best men’s henleys — and here’s how to do just that. For more tips on what to wear during snowy weather, check out the rest of my #OOTD series.

A classic henley helps tie everything together, does it not?

• The Henley: Flint and Tinder Organic Slub Henley, $45.98 — Get one of the best men’s henleys for a heck of a deal right now, then reap the benefits — Flint and Tinder knows how to make a rugged henley that’s perfect for layering. Speaking of …
• The Flannel Shirt: Portuguese Flannel Bravo Flannel Shirt, $91.98 — For chilly winter weather, you want nothing less than one of the best flannel shirts, especially in a pattern that’s elevated from the average.
• The Parka: Flint and Tinder Sherpa-Lined Waxed Ridge Parka, $297.98 — A tough waxed parka, especially the Flint and Tinder Waxed Ridge Parka with sherpa lining, is going to keep you warm and toasty, no matter how much time you spend outside (and with an outfit like this, made for outdoor excursions, that’s going to be critical).
• The Slim Chinos: Flint and Tinder 365 Pants, $98 — Yes, it’s a trio of Flint and Tinder style essentials to help this #OOTD along, but trust me: When you find slim tan chinos like these, you wear them as often as you can, all season long.
• The Boots: Nicks Boots Americana Boots, $529 — For navigating slippery city streets, pull no punches with the best leather boots — heck, simply some of the best boots for  winter, regardless of material or construction. Nicks Boots continues to outdo itself across the board.
• The Watch: Martenero Kerrison Watch, $595 — Now, you’ve seen the tough Martenero Kerrison Watch on the blog before, but it’s making a return today because it’s perhaps the best leather watch to have on your wrist all winter — it’s simply as premium as it gets.
• The Best Weekender Bag: Bespoke Post Weekender Box, $45 — Maybe you view this as the kind of ensemble to be worn for a rugged winter weekend away — or maybe not. But whether you’re hauling your everyday carry or hauling tools for a home project, the Bespoke Post Weekender Box has the carrying capacity you need.
• The Stylish Winter Hat: Wills Cashmere Ribbed Beanie, $75 — Now, who said your winter hat couldn’t be stylish and luxurious (even if the rest of your gear is rugged)? No, the Wills Cashmere Beanie begs to differ — staying warm this winter never looked so good.

Alright, so was that ensemble everything you thought it would be? When you kick things off the right way — with a rugged henley, mind you — the ability to layer stylishly and in rugged fashion for winter only gets easier. Of course, it helps to have one of the best flannel shirts on hand — especially from Portuguese Flannel in a pattern that’s a touch different from what you might expect. And because you’re not spending your winter indoors in the slightest, the Flint and Tinder Waxed Ridge Parka is here to help you brave the cold in style. Yet getting back to the sleek, go-anywhere ensemble you need, slim tan chinos are here to help save the day while keeping you office-ready. The whole look also gets a much-needed lift from the best leather boots, a pair that’s at home stomping through city streets and navigating slippery terrain on a weekend excursion — the more you wear ’em, the better your pair of Nicks Boots gets. Crucially, the Martenero Kerrison Watch is a must-have in your watch collection, given that it fuses bold style with durability and dependability — plus, it looks cool as heck on your wrist. And particularly when you step outside, the Wills Cashmere Beanie is everything you need in a stylish winter hat. For when you need to get out of town (Beacon, NY is a favorite winter weekend stop of mine), gear up accordingly with the Bespoke Post Weekender Box — it’s one of the best weekender bags for your must-have cargo. Where you go and what you do in this outfit is up to you, but rest assured: It’s absolutely ready for adventure. To see what else I’m wearing this winter, head to my Instagram.