#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

Men’s Style Holiday Wish List 2016

Editor’s note: Be sure to check out last year’s Men’s Style Holiday Wish List as you shop around. Portions of this post use affiliate links, from which a small commission might be earned. Thanks for supporting the brands that support The Style Guide!

If you peruse the pages of ye olde Style Guide regularly, you might recognize that your author is a big fan of the much-coveted style wish list. From a seasonal favorite — the rugged-leaning Fall Style Wish List — to holiday-centric picks like the ones below, it’s fun to shop around, look ahead and set goals. That is to say, the pieces featured below are definitely investment-worthy, often made with beautiful construction, quality materials and classic styling potential for the holiday season and beyond. It’s a favorite of mine to write, and hey, it’s fun to dream about what Santa might be putting under the tree this Christmas. You’ll recognize picks from Style Guide-approved digital sites like Huckberry and brands like Apolis, along with new picks sure to surprise, delight and possibly hurt your credit card. Not convinced? Read on below and drop us a note on The Style Guide Facebook page.

#1. Thorogood Dodgeville Boots in Cognac — $375


A handsome, rugged pair of boots made in America.

Who doesn’t love a pair of rugged leather boots? Very few, I’d say. And even fewer if the boots in question are the beautifully crafted, handsome-looking Thorogood Dodgeville Boots. They top this Wish List because, to be frank, last year’s Wish List featured leather sneakers at the top, and this year’s edition needed some refreshing — truly! Even more than that, they’re a unique change of pace from something like the Red Wing Iron Ranger — they’re unlined for a lighter weight and far less break-in time, and the Cognac color of the Dodgeville Boots should prove itself versatile, rich and investment-worthy — for you or someone else on your list.

Frank & Oak

#2. Todd Snyder Suede Quad Jacket in Tobacco — $1,595

A simply stunning jacket that's unique, premium and yes ... expensive.

A simply stunning jacket that’s unique, premium and yes … expensive.

So, first things first: Wow. Just … wow. That jacket is something else! And were it not for your author’s love of rugged, durable boots, it would top this list. Now, is it realistic to spend more than $1,500 on a jacket for yourself? Ehh… not really. That’s why it’s on the Wish List, though — it reflects the type of premium approach to heritage staples that Todd Snyder has perfected. From the Todd Snyder x Champion Pocket Sweatshirt to the stunning Suede Quad Jacket, each piece is worthy of the purchase price in its own way. This upgraded hybrid field jacket is one you should wear as much as you can — with a shirt and tie, over a marled henley and out to Sunday brunch this holiday season.

#3. Lum-Tec Special Edition Combat B30 Bronze Watch — $899.98

Uniquely durable, well-designed and long-lasting -- a beautiful watch for your own wish list.

Uniquely durable, well-designed and long-lasting — a beautiful watch for your own wish list.

Yet again, another entry on this Holiday Style Wish List is a jaw-dropper — at least for this #menswear fan.  Of course, it’s a jaw-dropper in terms of price as well as looks — the Lum-Tec Special Edition Combat B30 Bronze Watch is the type of watch that’s somewhat rare, in that it’s built for the field and the office in equal measure thanks to its handsome profile. The bronze case will take on a unique patina over time, the Miyota automatic movement is one of the best around, and the Combat B30 Bronze Watch  comes with four heavy nylon straps — the interchangeability means it could be dressed up with a leather strap, too. So yes, it made my wish list pretty easily — how about yours?

#4. Flint and Tinder Bomber Jacket — $178

A versatile, easy-to-layer and oft-coveted bomber jacket for the holiday style wish list.

A versatile, easy-to-layer and oft-coveted bomber jacket for the holiday style wish list.

Now, it’s somewhat rare that a piece like the Flint and Tinder Bomber Jacket — more suited perhaps for fall than winter weather — makes a cold-weather style wish list. But then again, the Flint and Tinder Bomber Jacket  is no ordinary bomber jacket. It’s tough, durable and fully ready for winter layering — it’s the rare bomber jacket that also nails the hybrid between casual and dressier style, so it could reliably stand in for a blazer atop a blue Oxford for unique (and toasty) looks. That’s what makes it a worthy addition to this list — the Flint and Tinder Bomber Jacket is high-quality enough to hang with the best outerwear around, and versatile enough to work through the spring. Heck, you might want to gift it to someone — and then pick one up for yourself.

<Join Frank & Oak Elevate - Enjoy FREE Shipping, Cashback + more at Frank + Oak! Try it now for 90 days, risk free!

A unique take on the trucker jacket in a winter-friendly fabric.

A unique take on the trucker jacket in a winter-friendly fabric.

We all love a versatile, durable denim jacket for the warmer months, right? And sure, you’ve got a tough waxed trucker jacket for the fall season. But what about when you need another casual layer during the chill of winter? Something to throw on underneath a slim topcoat or over a classic crewneck sweatshirt?  That’s exactly the type of jacket your friendly neighborhood menswear author had in mind when adding the Alta Wool Flannel Jean Jacket to this list – it’s unique in its silhouette and fabrication, cozy enough to wear over a marled henley with a winter scarf, and ready for prime layering this winter. Hopefully, Santa brings you one.


BONUS PICK: Apolis Selvage Denim Chore Coat — $228
Apolis Selvage Denim Chore Coat

A Huckberry exclusive made with the best denim around.

We’ve got a bonus pick for you here today, ‘cuz Santa doesn’t leave just one gift under the tree — does he? Brands like Apolis stock darn near all the great menswear you could ask for, from rugged picks like the Huckberry-exclusive Selvage Denim Chore Coat to classic staples like its Standard Issue Utility Chino. But the coat featured above is the one to grab — or covet — this holiday season. It’s made from premium Cone Mills denim in an immensely wearable silhouette, from the office to the trail and back. Again, I sure hope Santa hooks you up.
And with that, the book is closed on this year’s Holiday Style Wish List. Well, partially. On second thought, might just open up another tab for that Flint and Tinder Bomber Jacket … at any rate, it’s an exercise in fun that should get you thinking about gift-giving and saving ahead for the new year. Yes, we’re all about style resolutions, and upgrading key wardrobe essentials like a rugged chore coat and a stylish field watch are great goals to keep in mind this holiday season and beyond. Chime in on additions to your own wish list in the comments or on Twitter. And let’s connect via Instagram for plenty more menswear fun.
As always, thanks for reading!