#OOTD: How to Dress for a Casual Winter Weekend

Alright folks, here we go with another take on the #OOTD. There comes a time in your life when duty calls — when you want to get out of the house to head to brunch, or grab a cocktail, or pick up some more coffee, or reload for that home proejct — and it’s just got to be done in spite of the weather. That’s why we’re here: To tell you how to dress for a casual winter weekend, helped along by plenty of seasonal style essentials. The right winter weekend #OOTD ties everything together with functionality and style in mind — so, for fighting windy weather and snowstorms, you’ll find a rugged waxed jacket to take on the elements. Other layers come in handy once you’ve bellied up to the bar and taken off said jacket — take, for instance, one of the best new flannel shirts (more on that one in a moment). And classics like slim dark blue jeans never fail — inside or outside, coffee date or a quick trip into town. All these picks are more crucial than you think, including Red Wing Heritage boots for dependability and durability on slippery streets. The goal here should be gear picks that look great and don’t miss a beat from day-to-night, so you’ll also find crucial layers like one of the best men’s henleys. Check out the full look below, and let me know in the comments if you think we (and by we, I mean me) hit our goal. Cheers!

You’ll be able to go just about anywhere this winter with these rugged gear picks.

Ready to brave the elements? As taxing as that might sound at the moment, I know I am — it all comes down to starting with the right layers, and then building from there. In this case, the right layers just so happen to include a rugged waxed jacket that’ll fight off winter’s worst pretty handily. Layering a Faherty Brand flannel shirt is the right way to go for both warmth and style, plus a bit of versatility — that’s the sort of shirt you can wear to a casual lunch or a trip to your favorite bar in equal measure. You could also argue that if you’re not wearing a Taylor Stitch henley as your base layer, you’re not doing it right this season — that’s debateable, but there’s an argument to be made for making a rugged henley part of your menswear rotation. Naturally, Mott and Bow denim never fails in terms of style points or dependability — the same could be said for those go-anywhere Red Wing Heritage boots, all the better to beat out winter snow. Your accessories are also going to seal the deal here, from one of the best winter hats to a tough everyday bag that’ll keep your gear safe and sound. Of course, no look is complete without a rugged casual watch — that’s the right way to finish off this look. Where will this ensemble take you? Let me know on Twitter.

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