#OOTD: How to Dress for a Stylish, Casual Christmas This Year

There’s no time to waste this holiday season, which is why we’re talking today about how to dress for a casual Christmas. It’s coming up sooner than you think — VERY soon, in fact. If you still need a gift for your brother, dad, uncle, father-in-law — heck, any guy — check out this year’s men’s holiday gift guide. Oh, and before we get to today’s #OOTD, you’re going to need a gift for her: Check out this year’s women’s holiday gift guide right now (hurry!). Still need to dress for a holiday party? Check out this recent #OOTD. Now, to the main event.

Dressing for a casual Christmas should, first and foremost, be laidback and fun. After all, you’re likely spending the day around a warm fire, surrounded by good company and a few items off your men’s style wish list. Even if you find yourself away from your home (say, visiting your significant other’s parents), the below #menswear look is appropriately cool and easygoing — not sloppy. Trust me, getting you dressed in style for Christmas is a Style Guide tradition that goes all the way back to … this blog’s first year, 2013! Check out the OG post here. Now, as today’s look: It delivers the goods. From a standout denim jacket to fight off a brisk day to a casual T-shirt, stylish Taylor Stitch sweatpants and comfortable American Trench socks, every base is covered. Except for the gifts under the tree — that’s still on you. Happy shopping and enjoy these next few days in style!

The right mix of easygoing layers and casual style staples — Merry Christmas!

The Jacket: WP Standard Denim Jacket, $119 –This stellar denim jacket can be layered over a sweater or a tee with ease, and it lends a bit of rugged polish to this ensemble. Plus, it looks great to wear to a Christmas Day movie or a decidedly laidback brunch.

The Tee: Mott and Bow Heather Gray Crewneck, $32 — The makers of your favorite pair of jeans have now set their sights on the perfect T-shirt; the results are cozy, comfortable and more than ready for Christmas Day style.

The Pants: Taylor Stitch Travel Pants in Black Fleece, $88 — Suffice to say, we don’t recommend sweatpants too often here on the blog, but the Taylor Stitch Travel Pants are that rare pair of stylish sweatpants that manage to look more cleaned-up than sloppy. Go ahead, have another cup of cocoa & kick back by the fire.

The Sneakers: Gola Classics Harrier Woven Trainer, $90 — Now, if you happen to be dealing with a white Christmas, these classic and sporty sneakers might have to stay in the closet. But if not? These woven textile sneakers slip on and off with ease for holiday travel and holiday party-hopping.

The Socks: American Trench Kennedy Luxury Athletic Socks, $19.50  — Want stylish socks that combine a bit of retro, sporty style with comfortable fabric? That’s what the Kennedy Luxury Athletic Socks from American Trench can do for you. No socks with holes while padding around the house this season!

 The Briefs: Flint and Tinder Micro-Bamboo Boxer Briefs, $34 — The right underwear — like the Flint and Tinder Micro-Bamboo Boxer Briefs — can go a long way in keeping you comfortable while relaxing over the holidays.

The Watch: Form-Function-Form Horween Leather Chronograph, $118.98 (On Sale) — From the classic navy dial to the handcrafted leather strap, this Form-Function-Form leather chronograph (featuring Timex) is a winner when it comes to casual holiday style.

The Cap: Filson Watch Cap, $45 — Keeping warm and toasty is crucial if you’re dealing with cold weather this Christmas — the Filson Watch Cap accomplishes that in style.
Holiday 2017
And with that, I’ll leave you to all of your last-minute holiday shopping. Was this #OOTD helpful? Staying casual and comfortable, yet stylish, comes down to picking the right pieces and the right fabrics. Rather than reaching for slouchy, old sweatpants, throw on the  Taylor Stitch Travel Pants  for a pair of stylish sweats featuring significantly upgraded fabric and a tailored fit. When it comes to your T-shirt, swap in a tailored heather gray tee from Mott and Bow (or a classic chambray shirt, if you want to go just a bit more dressed up). Your footwear should be similarly versatile yet laidback, so textured sneakers from Gola nod toward the season in an easygoing manner — don’t forget sporty, stylish American Trench socks. Take it from me: They could be the last sock brand you buy. Winter accessories also can (and should) blend fashion and function — the  Filson Watch Cap is a great example of that approach. And to round out this casual look, a classic Timex watch offers both visual interest and situationally appropriate style. Before we go, don’t skimp when it comes to your undergarments; the Flint and Tinder Micro-Bamboo Boxer Briefs should be in your shopping cart now. If you’ve got any questions on how to dress for the holidays, be sure to hit me up on Twitter.

Thanks so much for reading, happy holidays and Merry Christmas!


Holiday 2017


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