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

Your search for the best winter style essentials — and more specifically, your search for what to wear during a casual Christmas this season — is coming to a close with today’s #OOTD. Or at least, that’s the goal of today’s post, anyways. The best gear for the holiday toes the line between casual and polished, and it’s anything but sloppy. After all, the holiday season can call for anything, from marathon football viewing sessions to unexpected dashes through the snow for craft beer, to a laidback brunch in town — mark my words, stylish sweatpants are going to work for all those situations (truly!), as will a rugged henley and more favorites as seen below (not to spoil anything, mind you!). These are pieces similar to gear you’ve already got, but with a few exceptions — namely, we’re ditching your old-school college tee (cozy as it might be!) for something that’s going to look good for hanging around the in-laws (or *gulp* future in-laws). Again, we’re striking a balance between cozy and relaxed, yet cool — hence, the handy indoor-outdoor boots shown below, paired up with the truly versatile Relwen Micro Pile Pop-Zip. Add to it all a rugged casual watch, a cozy beanie cap and some craft beer (and craft beer-themed reading!), and you’re all set to have the coziest, most stylish Christmas and holiday season you’ve had in recent memory.  If you like the look of this #OOTD, or have questions on how to dress for the holidays, check in with me on Twitter.

Cozy-yet-polished style essentials made for a casual Christmas (most of them from Huckberry). Cheers!

  • The Stylish Sweatpants: Todd Snyder x Champion Slim Jogger Sweatpants, $118 — Yes indeed, there is such a thing as stylish sweatpants, and for a casual, cozy Christmas, it’s hard to go wrong with Todd Snyder x Champion and these classic Slim Jogger Sweatpants.
  • The Henley: Flint and Tinder Raglan Waffle Henley, $62 — The right way to dress for a laidback day at home (or with family and friends) starts with a rugged henley. It’s a step up from your old athletic tee, it’s still put-together enough to dash out of the house, and above all, well, this is just one of the best men’s henleys for the season.
  • The Sweater: Relwen Micro Pile Pop-Zip, $168 — Although we’re keeping things very casual and easygoing, you’re still going to want a stylish, warm sweater to layer over your rugged henley, agreed? The Relwen Micro Pile Pop-Zip is assuredly the one to buy.
  • The Watch: Huckberry x Lum-Tec B44-H GMT, $595 — Make no mistake, the right casual watch can take your look from good to great – and yes, that’s the case even if you’re only hanging out at home. This rugged casual watch from a recent Huckberry x Lum-Tec partnership takes the cake.
  • The Slip-Ons: Greys Outdoor Slipper Boots, $108 — Alright, so are these Greys shoes … slippers? Or boots? Well, they’re both. Wear these indoor-outdoor boots around the house, wear them to stoke the fire on the back deck, heck, wear them to go pick up some more Anchor Christmas Ale. They’re some of the best slippers on the market for stylish guys like yourself.
  • The Hat: Topo Designs Watch Cap, $22 — Let’s say you only need to throw on this stylish winter hat to dash out to grab more firewood (or again, more Anchor Christmas Ale) — it’s still worth keeping handy.
  • The Essential Reading: “Drink Better Beer” by Joshua Bernstein, $18.99 — More on some excellent craft beer in just one moment, but if you or someone you love happens to be a beer aficionado and could use a truly insightful and fun craft beer read around the fire this year, pick up this book by beer expert and my Twitter pal Josh Bernstein. Cheers! Speaking of …
  • The Holiday Ale: Anchor Brewing 2019 Christmas Ale, Price Varies — The Anchor Christmas Ale, done in a new iteration every year, is a certified classic holiday beer (even if you don’t normally enjoy beer, it’s worth try a sip or two). This year’s brew features notes of cocoa and pine, plus rich, roasted malts. Guaranteed to brighten your Christmas, no matter what.

As I said earlier, we’re all about not skimping on proper style — even if you’re only hanging around the house or relaxing with friends and family. The beauty of this ensemble is that you could wear it out of the house without missing a beat if need be — the Todd Snyder x Champion sweatpants are nearly as well-cut as favorite pair of chinos, while the casual yet put-together nature of this #OOTD is on full display. That’s all thanks to one of the best men’s henleys for the season, plus the easy-to-layer comfort of the Relwen Micro Pile Pop-Zip — your old college hoodie, this is not. Lest we forget, whether you go with stylish socks or not, the surprisingly durable indoor-outdoor boots shown above are going to provide warmth, comfort & multi-faceted wearability. We’re going to tie everything together with a rugged casual watch from Huckberry x Lum-Tec, to go along with a weather-ready, stylish winter hat. And because you’re going to need something to sip on — and read — around the fire, why not reach for the exceptionally delicious Anchor Christmas Ale while thumbing through “Drink Better Beer” by Mr. Bernstein. Both are guaranteed to go over very well. Taken altogether, I’d say that once again, you’re going to have your most stylish Christmas yet. Cheers!

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