#OOTD: How to Dress for a Warm, Stylish Winter Weekend

We’ve talked in past weeks on the blog all about how to dress to really get out there and explore for fall and winter, from the best way to wear a henley to how to wear an Oxford shirt to the office (and beyond. Today though, we’re taking a different point of view — namely, we’re covering exactly what to wear on that first really chilly, really snowy fall or winter weekend, the kind of weekend where you don’t want to (or can’t!) leave the house … and it’ll be here before you know it, trust me. More specifically, we want you to be ready when it does … even if being ready involves bundling up in cozy essentials like the Faherty Brand Blanket-Lined CPO as you hunker down around the fire, book in hand. But as I always say, just because the day is spent inside with your significant other (or totally on your own), doesn’t mean you should dress like a slob. Far from it — this #OOTD is all about how to dress casually and cozily while keeping style in mind. Witness the¬†Flint and Tinder Heavyweight Henley, as stylish a layering piece as it gets, along with the pleasingly slim Grayers Athletic sweatpants. Heck, we’ve even got a stylish casual watch in the mix. Throw in warm house shoes, a trusted book and your favorite tunes via a stylish Bluetooth speaker, and you’ve got your fall and winter day or evening plans taken care of. Again, this look is a slight upgrade over your normal off-duty garb, and that’s something worth applauding. With the holidays coming up, I’d even say you should feel comfortable wearing this cozy ensemble around family at the cabin or after a day on the slopes. It’s that stylish — find it below, then feel free to connect with me on Twitter if you end up wearing any of these winter style essentials.

All the gear you need to stay cozy, warm & stylish this winter.

  • The Overshirt: Faherty Brand Blanket-Lined CPO, $168.98¬†— It helps fight the chill when your stylish winter shirt is also a jacket, and it helps even more when it’s done in rich indigo. a la this handsome Faherty Brand piece.
  • The Henley: Flint and Tinder Heavyweight Henley in Natural, $62¬†— Feel free to layer whatever you’d like underneath your stylish indigo overshirt … but for my money, the¬†Flint and Tinder Heavyweight Henley¬† is the way to go.
  • The Stylish Sweatpants: Grayers Athletic Palmer Fleece Joggers, $88¬†—¬† Hey, every guy needs a pair of easygoing pants that aren’t jeans or chinos … or pajama bottoms.¬† The slim, surprisingly stylish Grayers Athletic sweats seen here are a major sweatpants upgrade.
  • The Watch: Timex Archive Waterbury United Watch,¬†$120¬† — Ever so slightly rugged and ever so slightly refined, the Timex Archive Waterbury could turn into your go-to everyday leather watch.
  • The Stylish Slippers: Giesswein Andau House Shoes,¬†$98¬†— Available in men’s and women’s sizes, these house slippers channel a bit of menswear thanks to the charcoal boiled wool upper. A much more stylish pair of slippers than you might be used to — and fitting for padding around your house or cabin.
  • The Evening Cocktail: Naked Grouse Blended Scotch Whisky,¬† About¬†$33¬† — I’ve had the chance to try this Naked Grouse whisky over these past few weeks, and it’s got a flavor and richness to it unlike any other spirit I’ve had. A nice way to unwind in front of a roaring fire.
  • The Audio Essential: Cavalier Portable Speaker,¬†$254.98¬† — Life is about the simple pleasures, like listening to your favorite band (*cough*¬†The National¬†*cough*) on a chilly fall or winter evening, whiskey in hand. This¬†stylish portable speaker¬†upgrades the experience.
  • The Finishing Touch: Bespoke Post Dwell Box, $45¬†— Complete with a cozy blanket and some nice incense, the Bespoke Post Dwell Box is the right way to complement a day or night in.

I’m always an advocate for putting your best foot forward, even if you happen to be lounging around the house catching up on Netflix or diving into your favorite book. And when the situation also calls for staying warm and cozy, well, you’re not going to find a better blend of the two than with the rugged¬†Faherty Brand Blanket-Lined CPO¬†and the equally rugged, warm¬†Flint and Tinder Heavyweight Henley. While you could easily swap in a pair of slim stonewashed jeans if you wanted to, the¬†Grayers Athletic sweats¬†are comfortable without being sloppy. The same can be said of the boiled wool house shoes as seen above — another upgrade from traditional fuzzy slippers. And when you’ve got the whole day in front of you at home, it helps to stay on time — that’s where the exceptional Timex Archive Waterbury United Watch¬†is going to come into play. The rest of your accessories are as essential as can be when staying in for the day, from a¬†stylish Bluetooth speaker¬†to the warmth of the¬†Bespoke Post Dwell Box.¬†And if you happen to be looking for a cocktail to enjoy in the midst of this? Best go with a new, beautifully done whisky from Naked Grouse.¬†Tell me: How do you dress for a day or night in? Do you agree with this #OOTD?

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