Style Suggestion: A Cozy Christmas

Editor’s note: For more Style Suggestions — including what to wear to that holiday party — swing through here.

Breaking news — Christmas is almost here! If you’re a big fan of the holidays, like me, and appreciate a festive atmosphere in the air and lights all around the cityscape (or your hometown), there’s really no better time to enjoy. But thankfully, the holiday also gives everyone a chance to rest, regroup and ideally, actually get home for some time off. Either way, Christmas and the events surrounding it don’t always have a set dress code — it could be a more casual evening of opening gifts with just the family, or a nice party with friends (hopefully, Ryan Gosling doesn’t drop by). So the style suggestion that follows definitely errs on the side of more casual, whether this is on Christmas Day itself or in the days leading up to. Bear in mind — this is just one suggestion to keep things from getting too sloppy, so mix-and-match (and buy) as you please! Note that we’ll cover a more dressed-up Christmas affair right here next week.

The Shirt: Tommy John Ringer Pocket Tee in Heather Grey — $34

This colorblocked pocket tee is a simple but effective upgrade from the pedestrian crewneck.
This colorblocked pocket tee is a simple but effective upgrade from the pedestrian crewneck.
So right off the bat, that price is a bit much more than most might pay for a T-shirt. BUT, bear with — Tommy John certainly seems to be the real deal as far as quality and comfort goes in the undershirt and T-shirt game. And its Ringer Pocket Tee (available in four colors) is soft, stylish and slim-fitting. Crucially, the color at the neck and pocket sets it apart just so slightly from a regular crewneck tee, even when that might be the cheaper option.  It’s these small style upgrades that can add a little thought to your look, and if comfort is part of the equation, it’s key to still look good. However, if wearing just a tee makes you wary, I’d reach for a great chambray shirt instead.

The Sweater: Old Navy Chunky Shawl-Collar Cardigan — $49.50 (When On-Sale)

A rich color and ribbed knit make this a solid house sweater for a cozy Christmas.
A rich color and ribbed knit make this a solid house sweater for a cozy Christmas.
Because it’s the heart of December, we’ll assume it could be a little bit chilly wherever you might be. That’s exactly the time to reach for a well-priced Old Navy cardigan. The burgundy color is a nice, on-trend nod to the season as a whole (although this cream JackThreads Shawl Cardigan could also be a neat, affordable pickup). But in this instance, the thick burgundy knit brings some nice contrast when paired alongside the lightweight T-shirt. As I’ve said time and again, a shawl-collar cardigan is a great, masculine style move that adds some rugged appeal to any outfit. Plus, who doesn’t love a cozy sweater? If it’s too warm out where you are, ditch it (if you’re lucky enough, that is!).

The Pants: JackThreads The Daily Jogger — $49.50 OR Classic Dark Denim

A dark color and trim cut help these wear less like sweats and more like jeans. Yes, you got that right.
A dark color and trim cut help these wear less like sweats and more like jeans. Yes, you got that right.
As we talked about above, Christmas can go one of two ways — more casual, or dressier. In this case, if you’ve got the option to go more laidback yet want to avoid wearing pajama pants, we’re going out on a limb to recommend a pair of tailored sweatpants in a dark color. JackThreads continues to get a lot of things right with its new menswear line, and stylish essentials at low prices like these are why. Again, if sweatpants still feel too casual, a solid pair of dark denim never fails (I’d recommend Mott & Bow, who makes slim jeans like its Hester model with a comfy hint of stretch). If sweats are too hot, reach for their laidback but just as comfy alternative — the well-crafted sweatshort (like these from my friends at Pistol Lake).

The Sneakers: GREATS Brand Royale Chukka — $152 (On-Sale)

Camel plus black in a chukka silhouette = dressier sneakers than the norm.
Camel plus black in a chukka silhouette = dressier sneakers than the norm.
If sneakers seem a silly option for the middle of winter (and they very well might be if there’s a ton of snow), I’d urge you to go with a reliable (but cheaper) desert boot instead. If, however, you’re able to rock some chukka sneakers from GREATS, you’ve found a style choice that fits right in with fall & winter yet feels more comfortable than a thicker boot (note that Reef’s Outhaul Lux Chukka does that, too). The Royale Chukka definitely checks all those boxes, and even more crucially, the camel color plus black sole is a combo that feels a little dressier than a plain pair of captoe sneakers. These sneakers can be worn through the rest of winter in the right weather, and into spring with some lightwash jeans, too — that’s the gift that keeps on giving.

The Watch: Timex Weekender 40mm — $46

A black leather strap and that simple Timex dial create the ideal happy medium for the rest of this outfit.
A black leather strap and that simple Timex dial create the ideal happy medium for the rest of this outfit.
Just as in this site’s Thanksgiving Style Suggestion, a Timex is the affordable watch pick once again. In this instance, Timex’s classic weekender dial keeps the watch more casual, but the black face and slip-thru black leather strap makes it ever so slightly put-together. Yet, it’ll still look right at home with this outfit in terms of color and styling potential — it’s just that simple and versatile. Lest we forget, this watch can be mixed and matched with other NATO straps — that’s like getting a new watch for about $10.

The Socks: Richer Poorer Herald Socks — $12

A small way to pump some pattern into an outfit -- for a low price.
A small way to pump some pattern into an outfit — for a low price.
Whereas the rest of this outfit mainly sticks to solid basics, these socks inject some life into the ensemble in a fun way. And assuming you’ll be kicking around without shoes on for a bit, clean, hole-free socks are a must (truly). Throw in a fun polka-dot pattern in a color that complements the rest of the outfit, and you’re set. The oatmeal color of these socks is also just different enough if you go with a heather-grey T-shirt (or even a blue chambray), and the navy dots complement the cardigan and the sneakers, too. Plus, Richer Poorer socks are springy and breathable — not a  heavy wool set.

While the above outfit might not work for everyone, here’s hoping you do get the chance to kick back in a more casual fashion this Christmas — and when that time comes, I hope you’ll keep some of these picks in mind (because who doesn’t love looking their best all the time?). Think I missed anything? Let me know your picks for the holiday season below!

Ben Sherman US

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