#OOTD: How to Dress for the Holidays This Year, At Home or On The Road

It’s been the theme of these last few weeks and months: Chiefly, the holidays are going to be mighty different this year, to say the very least. And yet, dressing for the situation and dressing the right way are still tentpoles you can hang your hat on, and that’s why we’re talking about how to dress for the holidays in style — at home or on the road. Hosting a handful of people, hitting the road for a distanced getaway or Zoom-ing through the holidays, getting cleaned up is a small way you can seize the occasion the right way, no matter how different things might look. That’s why today’s #OOTD has everything you need to blend comfort, travel-ready versatility and long-term style in one ensemble. From a comfortable and stylish overshirt to your new favorite henley, the bases are covered when it comes to casual layers. And as you’ll soon see, stretch pants get the job done for holiday dinners, days on the couch and days behind the wheel. The same can be said for stylish slip-on sneakers and premium men’s socks, not to mention one of the most affordable weekender bags (if you do decide to carefully hit the road, that is). Although your plans are probably different than expected, keep in mind that dressing for the occasion is one way to make things more normal — wishing you all the best this season, and scroll on through for the full look below.

The right casual style picks for the holiday season, to say the very least.

  • The Overshirt: Faherty Brand Legend Sweater Shirt, $178 — Wear this laidback-yet-polished shirt on its own or layered up accordingly. Just know that it’ll look polished for hanging out at home, hopping on a Zoom call or hitting the road.
  • The Henley: Flint and Tinder Heavyweight Henley, $62 — Ideal for lounging at home or wearing as a base layer on a cold evening in front of the fire, this is one of the best men’s henleys out there, folks.
  • The Stretch Pants: Western Rise AT Slim Pants in Sand, $128 — Comfortable stretch pants that feature durable fabric, a tailored fit and polished-yet-functional style? Sounds perfect for the holidays to me.
  • The Sneakers: GREATS Wooster Suede Sneakers in Olive, $149 — Because you’re likely either traveling by car or hanging at home (or keeping it casual with a small group of family), some stylish slip-on sneakers are a nice upgrade from slippers themselves, but without the formality of dress shoes.
  • The Watch: Lum-Tec M88 Watch, $575 — Go with a rugged-yet-easy-to-wear leather watch that toes the line between too casual and too formal, then wear it to plenty of small holiday gatherings.
  • The Socks: American Trench Cashmere Athletic Stripe Socks, $119.50 (Three-Pack) — For padding around your house or someone else’s, get these premium men’s socks (and more than one pair, at that) for the holiday season.
  • The Getaway Bag: Boarding Pass NYC “Work Hard, Play Hard” Duffel, $79 — If you do end up hitting the road, use the code BEAUKNOWS to get $10 off your purchase of $70 or more. That makes this bag one of the most affordable weekender bags on the market.
  • The Grooming Essential: Jack Black “Jack’s Most Wanted” Grooming Kit, $65 — No matter whether you hit the road or stay at home, keep your face looking fresh as can be with one of the best men’s grooming kits.

Now then, who’s ready for the holiday season? And in a different way than before, perhaps? You might have planned on rocking sweatpants (not a problem if they’re stylish ones!) but this #OOTD, to me, steps things up just a notch while keeping comfort and great looks at the forefront. It’s all about looking as best as you can while reading the room (sometimes literally!) the right way. To wit: The Faherty Brand Legend Sweater Shirt is always available when you want to add some casual polish to even a rugged henley, while some comfortable stretch pants deliver the great looks of chinos with the fit and feel of, yes, sweatpants. Your stylish slip-on sneakers work well on the road or at home, and it’s best to pair them up with premium men’s socks when the time does come to slip off those shoes. Packing up just got a whole lot easier thanks to one of the most affordable weekender bags, and no matter where you go, you’re destined to look great if you pack up (or simply purchase!) one of the best men’s grooming kits. It’s all accounted for in this holiday-ready #OOTD, so make sure you rise to the occasion this season. Stay safe and thanks for reading!

#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!

#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!

-Beau

Holiday 2017

#OOTD: Dressing for a Casual Christmas

Editor’s note: You’ve surely seen this hashtag lots of different places, including on Instagram. But how does that carry over to real life? The #OOTD series will take one great item and put together a versatile, stylish outfit around it. Look for past features here.

OK, so we’re coming at you with a Thursday edition of the #OOTD series. Namely, we’re just a few days out from Christmas — that came up quick, yes? Hopefully, you turned to The Style Guide (or another one of your favorite menswear blogs?) to knock out your holiday shopping. Still need a gift for her? Fear not. Or maybe you want to add an item or two to your holiday men’s style wish list? Easy does it. Oh, and that leaves another crucial question — what are you going to wear for the occasion? Whether you’ve got one last holiday party to dress for or if you’re approaching the day with a bit more formality, we’ve got you covered when it comes to dressing for Christmas. And that’s why today’s #OOTD covers another potential holiday style scenario: the casual holiday. Maybe you’ll be spending the day at your house and venturing out later for a movie or a drink with friends, or perhaps you’re taking it easy while on a holiday trip over the river and through the woods– either way, dressing with some polish is key. We’re not talking about going overboard — leave the velvet dressing gown at home. No, we’re talking about a crisp, casual outfit that looks stylish, fits great and is a bit better-suited for venturing out in public than your pajamas. If you choose to stay in your PJs all day — hey, nothing wrong with that. But if you want to look a bit more cleaned up while still feeling comfortable? I’m your guy … or rather, the below #OOTD is the one to shop.  Chime in over on Twitter if you’ve got questions, additions or deletions when it comes to this look. Hit me up on Instagram if you want to see how I’m styling my Christmas Day #menswear picks, while we’re here.

Cozy, casual, comfortable and yet ... quite put-together.

Cozy, casual, comfortable and yet … quite put-together.

The Cardigan: Abercrombie & Fitch Belted Shawl Cardigan, $75 –We’re kicking things off with a really unique, effortlessly stylish sweater from the new and very improved Abercrombie & Fitch — the Camel color is eye-catching and pairs nicely with our other casual picks.

The T-Shirt: Barking Irons Brando Tee, $49 (2-Pack) — You could always reach for a classic chambray shirt if you wanted something a bit more cleaned up, but a textured cotton tee with unique design details — like a scalloped hem and slightly raised sleeves — is a cool, effortless pick.

The Denim: Mugsy Jeans Kinzie Denim, $98 — Who said denim has to be uncomfortable? Mugsy jeans are built with more room in the crotch and a ton of flexibility for a great — plus, the light wash is more casual, and these jeans look a bit more crisp than tailored sweats.

Beckett Simonon

The Watch: Timex + Todd Snyder Red Wing Leather Chronograph in Grey, $158 — Even if you’re just hanging around the house, it can be fun to throw on a stylish casual watch — especially one from Todd Snyder.

The Belt: J. Crew Factory Braided Leather Belt, $29.99 — Let’s keep it casual on the accessories front — a trusty braided leather belt is comfortable and mixes in some cold-weather texture.

The Socks: CHUP Churro Socks, $35 — Limited edition, nature-inspired prints on a comfortable pair of CHUP socks? Sign me up. They’re pricey, but very well-made and eye-catching — perfect holiday style, in short.

The Sneakers: SeaVees White Walls Mid-Cut Wintertide Sneaker, $98 — Sneakers in the winter? Yes, sir. You can always grab a pair of durable leather boots if snow is in the mix, but if it’s simply a bit chilly? These casual-yet-crisp mid-top sneakers are made with navy flannel fabric and blend right in with this ensemble.

The Grooming Kit: Harry’s Deluxe Truman Set, $35 — Just because it’s a casual Christmas doesn’t mean you shouldn’t get cleaned up a bit, ehh? This deluxe shaving set has everything you need to look great through the new year.

OK, we’ve got your unique, modern and comfortable belted cardigan, your classic T-shirt and slim stretch denim. Those are the building blocks of a nice cold-weather casual ensemble  in fall or winter, yet they work particularly well for lounging around — yet looking great — this holiday season. When you complement those pieces with a durable leather watch and a pair of premium patterned socks, you’re set with a look that’s versatile and sharp. Navy flannel sneakers are a unique finishing touch, too. Of course, putting in a little extra effort when it comes to winter grooming essentials is a solid move, too — and if you happen to be spending some time with your significant other on Christmas, they’ll appreciate it. How will you be dressing for a casual Christmas? Or do you still have some holiday shopping to finish up before you worry about what you’re wearing? Again, check out our women’s holiday gift guide for quick and easy picks.

Stay stylish and enjoy the season!

-Beau