#OOTD: How to Dress for Your Next Holiday Party This Year

Now, I know what you might be thinking if you’ve got a boatload of holiday party invites: Well, what the heck am I going to wear to this thing? Dressing for your next holiday party isn’t quite as much of a chore as it might seem — that is, if you know where to start, and if you go into said holiday party with an open mind. Whether it’s your office get-together or a small dinner with friends, or a crosstown jaunt to a holiday house party, today’s #OOTD tackles what to wear to a holiday party … the right way, and with ease. To wit: The season should be fun, so throw on a stylish winter blazer, ditch your regular office-hours suit (as stylish as it might be), and step out in a classic flannel shirt, to boot. These picks are accessible and sharp, yet versatile enough for other occasions (if you’ve got a black tie holiday party, then you might want to stuck with that dress code). It’s all about stepping things up accordingly and working with what you’ve already got in your wardrobe, so you’ll also find some stylish Chelsea boots and a sharp leather dress watch along for the ride. We’re not going too far over the top, so this look is anything but stuffy. Crucially, we’re also avoiding a loudly patterned sweater — save that for, well … maybe just leave that one tucked in your closet. There are no novelties or gimmicks in sight here, just a great blazer, slim corduroys and other winter style essentials aplenty. OK, it’s time to get ready. Cheers!

The right combination of refined and accessible for your next holiday shindig.

  • The Blazer: Outerknown Ambassadoar Blazer, $325 — With its soft wool construction and easygoing-yet-polished silhouette, this stylish winter blazer is a surefire holiday party hit.
  • The Shirt: Corridor NYC Check Flannel Shirt, $135 — You’re investing in the best with, well, one of the best shirts for winter. The check pattern is strong and unique, perfectly suited for a chilly winter’s night and perhaps, a sip or three of the best Old Fashioned.
  • The Pants: Flint and Tinder 365 Corduroy Pants, $98 Slim corduroy pants in a rich winter color are about as good as it gets when it comes to holiday party style, right? Right. Flint and Tinder knows how to craft a mighty fine pair of stylish corduroy pants, indeed.
  • The Dress Boots: Rhodes Footwear Huxley Boots, $220 — Sleek, stylish Chelsea boots hardly ever go wrong — especially at a holiday party where the vibe leans more tailored and less casual. And even if you’re heading over to a friend’s house & ditching your shoes at the door, well, these Rhodes Footwear boots still deliver style and functionality the rest of the evening.
  • The Socks: CHUP Montana Socks, $35 — Don’t underestimate the style and power of a great pair of men’s socks, especially if you’re going to be slipping of your shoes at someone’s home. The small details matter, and CHUP assuredly makes some of the best men’s socks on the planet.
  • The Watch: Carpenter Watches G-4 Brooklyn Gent Watch, $724.98 — WIth a crisply tailored yet accessible #OOTD like this one, the best dress watch can make all the difference. And no matter where your holiday party happens to be, you want to look as sharp as possible — Carpenter Watches reliably knows this.
  • The Gloves: Hestra John Gloves, $150 — Staying warm no matter what is critical as you head to your next holiday party — don’t leave home without a pair of the best men’s leather gloves from Hestra, ya dig?
  • The Host Gift: Michter’s US 1 Toasted Barrel Finish Sour Mash, Price Varies — Although you might be more apt to keep this Michter’s whiskey for yourself — and it’s a prime pick-up if you’re hosting a holiday party — this is a fine and seriously premium whiskey for the true aficionado, made with a unique aging process using toasted barrels. The result is one of the best new whiskeys for the season, easily.

Maybe to you, dressing for your next holiday party doesn’t look that much different than any other set of winter style essentials you might find yourself wearing. But in the season of good cheer and giving thanks, it’s all about how you carry yourself, enjoy the evening and also, pull everything together. So the casually rugged flannel shirt you reach for on the weekends can pull double-duty here as a suitably stylish office party shirt, while the stylish winter blazer from Outerknown shown above is well-suited for both the office and post-work day festivities. Heck, you can even add a tie if you  need to step things up a notch, and your stylish corduroy pants also work quite nicely at the office and at that holiday party. For getting to and from the party, you’ll be staying light on your feet AND looking sharp to boot in a pair of stylish Chelsea boots, nicely complemented by some of the best men’s socks for the season — seriously, the small details matter. Because we’re going all-out, you’re going to be wearing the best dress watch on the market (at least, for less than $1,000, that is). Your accessories continue to make all the difference, too, thanks to some of the best men’s leather gloves from Hestra — you won’t miss a beat on any fronts. And whether you’re slinging cocktails with the boss or gifting your host, a bottle of truly excellent Michter’s whiskey never fails. That, to me, represents the perfect ensemble for the season — if you agree, let me know on Twitter! Thanks for reading, and happy holidays!

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