Editor’s note: You’ve surely seen this hashtag lots of different places, including on Instagram. But how does that carry over to real life? The #OOTD series will take one great item and put together a versatile, stylish outfit around it. Look for past features here.

So, welcome back to the #OOTD series here on The Style Guide. The above headline might seem a bit familiar — after all,  a slim crewneck sweater is a personal favorite of this blog, and it’s as well-suited for casual, rugged fall style as it is for layering in the early stages of winter. And the particular sweater that’s being featured today is as close to a perfect reinterpretation of a classic style as we’ve got — especially from lauded American menswear designer Todd Snyder. But what differentiates the below #menswear look from other features here on the blog? We’re throwing in more weather-ready layers, for one. And we’re mixing high-low style staples like a slim topcoat with everyday wardrobe staples. If you find you don’t have any of the picks below, it’s as good a time as any to get shopping. Got additional picks to add to the below list? Hit me up on Twitter, or check out the Instagram feed for a look into what makes The Style Guide (AKA, me) tick.

A high-low way to wear a crewneck sweater this winter. Not bad, ehh?

The Sweatshirt: Todd Snyder x Champion Pocket Sweatshirt, $98 — The Todd Snyder x Champion line is packed full of stellar, heritage and sportswear-inspired pieces. This Pocket Sweatshirt is exhibit A in  that regard — it’s comfortable, easy to layer and potentially your new favorite sweatshirt.

The Shirt: Life/After/Denim Windom Oxford Shirt, $128 — More than $100 for a classic Oxford shirt? Well, when it’s made from premium yarn-dyed cotton in a slim cut, it’s worth the investment.

The Topcoat: JackThreads Tieman Topcoat, $149 — So, here’s where a bit of that high-low style comes into play. The “topcoat-over-a-crewneck” look is something perfected by the likes of David Beckham, so I’d say it’s Style Guide-approved.

The Denim: Buck Mason Black Slim Stretch Denim, $175 — From the makers of your favorite short-sleeve chambray shirt comes a fantastic pair of slim black denim — just as ready for a  rock concert as a casual weekend coffee date. What belt to wear? Well, brown and black can work casually (keep reading), so reach for a braided leather belt.

The Socks: American Trench Fair Isle Sock in Merino/Cashmere, $28.98 — So, some of the picks in this particular #OOTD are quite pricey — including these socks. But American Trench does things as well as anyone when it comes to stylish, durable accessories.

The Boots: Thorogood Dodgeville Boots in Cognac ,$375 — Need another pair of durable, rugged leather boots in your closet? This handsome, versatile and easy-to-wear unlined pair of Thorogood Dodgeville Boots are a nice way to amp up the slightly more casual crewneck sweater.

The Watch: MVMT Watches Calypso Watch, $145 — From the stellar new Modern Sport Collection by MVMT Watches, the Calypso is a particular highlight. It’s got the handsome look of a rugged Tudor watch at a fraction of the price. Since it’s a casual outfit, a black rubber strap can work alongside the cognac Thorogood boots.

The Hat: Columbiaknit Marled Watch Cap, $17.98 — Sometimes, you don’t need to go too fancy with your winter accessories. In this case, the Columbiaknit Marled Watch Cap is neutral, simple and quite functional in the cold.

And, well, that’s all she wrote. When it comes time to layer up on a casual-but-cold day at the office or around town, you nearly can’t beat a stylish crewneck sweater — especially one made from premium materials. And pieces like slim black denim and a classic navy Oxford create a bit of a unique one-two punch, particularly when accented by an affordable (yet great-looking!) camel topcoat. When you top it all off with rugged, eye-catching cognac leather boots, it’s a mixture of pleasing colors and textures that work well when put together (yes, even the black denim and brown boots). Of course, you can’t go wrong with a warm winter hat or well-made Fair Isle socks. In fact, this head-to-toe look might just become one you break out time and again — at least, I hope so.

Stay stylish, and stay tuned for a (relatively) last-minute holiday gift guide coming tomorrow.

Thanks for reading!

-Beau