#OOTD: Here’s The Best Way to Dress in Tough Winter Style

My friends, I can barely believe it … but it’s time for the first #OOTD of 2018 here on The Style Guide! That’s pretty monumental, if you ask me. And you can rest assured that we’ve got more of the same great content on the way this year as in years past — particularly if you want to dress in weather-ready style. It’s time to bundle up and fight the chill, without sacrificing any comfort or good looks. Think of it like dressing for the polar vortex … but without the doomsday aspect of extreme winter weather. Rather, the below #OOTD is designed to get you from point A to point B without any fuss, from weekend errands to a weekend dinner with friends. Start out with a tough winter jacket from Iron & Resin, keep things going with a stylish pair of brown leather boots, add your new favorite henley … and get ready to take on the winter weather. The below #OOTD has everything you need … at least, I think so.  Let me know what you think of this look on Twitter or in the comments. Stay warm, stay stylish!

From a classic winter jacket to a tremendous pair of leather boots, this is the gear to get you through winter reliably … and stylishly.

The Jacket: Iron and Resin Barracks Jacket, $342.98 — With a silhouette that echoes a classic field jacket, plus a weather-ready Melton wool exterior, the Barracks Jacket from Iron and Resin is versatile and rugged.

The Henley: Flint and Tinder Heavyweight Henley, $62 — What’s better for braving the cold than a rugged henley? Especially one from Flint and Tinder, a favorite of this blog? Feel free to add a stylish flannel shirt over this Flint and Tinder henley if you need more warmth.

The Denim: Flint and Tinder Dark Indigo Jeans, $118 — We’re going again with more Flint and Tinder gear, this time a dependable pair of classic blue denim featuring the brand’s new dark indigo wash. Durable, rugged and USA-made.

The Boots: Oak Street Bootmakers Brown Dainite Sole Trench Boots, $462 — It’s always tough to narrow down your pick of boots for the winter weather, but these fantastic Horween leather Dainite Sole Trench Boots from Oak Street Bootmakers are a pretty darn easy choice. Stomp through snow all ya want.
The Belt: Filson Leather Belt, $85 — The right belt for tackling winter weather isn’t a braided cotton belt that you’d wear during the summer … it’s a rugged, well-made Filson Leather Belt. No bones about it!

The Watch: Military Watch Co. MIL-TECH MKIV Military Pilot’s Chronograph, $330 — Just as you can’t skimp on your rugged winter boots, you can’t skimp when it comes to your watch game — although the name is a mouthful, this Pilot’s Chronograph should serve you well in the snow.

The Socks: CHUP Dia Socks, $28Stylish patterned socks should be a go-to in any season — the fact that the CHUP Dia Socks just happen to be cozy and comfortable is a big bonus.

The Beanie: Finisterre Fisherman Beanie, $40 — Again, we’re not just going with any beanie cap here … we’re going with a dependable-as-heck Finisterre Fisherman Beanie. Good enough for the water, good enough for you.
 If a winter storm catches you by surprise, or a bunch of snow gets dumped on you unexpectedly, it’s best to have the right gear in your closet to get you through. To me, that means the Barracks Jacket is one to reach for when things get dicey, yet you still want to look put together. Dependable footwear also goes a long — the Dainite Sole Trench Boots from Oak Street Bootmakers are positively stunning and well-crafted, ready for winter snow. Supporting accessories, from that tough Pilot’s Chronograph to warm CHUP Dia Socks, are equally underrated yet essential. For the rest of the winter season, I wouldn’t leave home without the  Finisterre Fisherman Beanie or a dependable mid-layer like the Flint and Tinder Heavyweight Henley. And although they’ll work reliably throughout the rest of the year, the Flint and Tinder Dark Indigo Jeans are a great go-to when it comes to stylish blue denim for winter. Are there any picks you particularly agree with? Disagree with? Chime in via the comments below — thanks for reading!


#OOTD: How to Style a Crewneck Sweater This Winter

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?

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!