#OOTD: Wear This Gear for the Perfect Thanksgiving This Year

Worried about what to wear to Thanksgiving? Worried you’re running out of time to put together an ensemble packed with fall style essentials? Folks, you’ve still got at least some time to get things together — and if you’re already on the road or packing up with one of the best weekender bags, well, consider this #OOTD some handy style inspiration all the same. Thanksgiving is a time to relax with family and friends, reflect on a year well-lived and enjoy some (hopefully) crisp and cool winter weather in style. That being said, the below Thanksgiving #OOTD is all about casual-yet-polished comfort and style — these are the kind of picks you can mix and match (from an American-made flannel to a stylish wool blazer), yet they’ll also look just right on your own. The key here comes in not overthinking it …  but in putting forth some effort all the same, even for a quick crosstown jaunt. In fact, the blazer featured below (from casual style masters Outerknown) could be the blazer to wear for Thanskgiving. And yes, we’re recommending you wear a blazer — we’re going cool and casual, but not sloppy. So, you’ll also find a pair of sleek Chelsea boots up for the taking, to go along with a stylish leather watch — the details matter, without a doubt. This look works for travel to your destination, plus a meal at home, and you can also repurpose the rugged flannel shirt to wear on Wednesday (the biggest bar night of the year, after all, ehh?). And for travel, the Outerknown Ambassador Blazer has plenty of space for your everyday carry, too. Think of this as a multifaceted, versatile & polished #OOTD  that works at Thanksgiving and throughout the holiday season — but first and foremost, let’s get you ready for the holiday. Don’t forget the pumpkin pie! And have a great holiday weekend, folks.

It’s never too late to put together the perfect #OOTD for Thanksgiving.

The Best Basics. Summer Ready.

  • The Blazer: Outerknown Ambassador Blazer, $325 — Is it too late to find the best blazer to wear for Thanskgiving? Not quite! Made with sustainable, unlined construction and featuring a tailored fit, this is the perfect casual blazer — not stuffy or uncomfortable in the slightest.
  • The Flannel Shirt: Flint and Tinder American-Made Flannel, $98 — While a rugged flannel shirt won’t work in warmer climates (simply swap in a stylish merino tee), this American-made flannel is as classic as it gets for the season. Plus, it looks great when you roll up the sleeves and shed the Outerknown Ambassador Blazer.
  • The Denim: Todd Snyder Slim-Fit Stretch Selvedge Denim, $198 — Want style that’s laidback and yet polished? Turn toward Todd Snyder’s selvedge denim — yes, you can wear jeans on Thanksgiving, especially if they’re made from rich Japanese selvedge fabric in a pleasing wash.
  • The Chelsea Boots: Rhodes Footwear Huxley Boots, $220 — For ease of getting to and from Thanksgiving dinner, and for equal parts functionality (traction on slippery roads) and style (sleek Chelsea boots never fail), reach for Rhodes Footwear this season.
  • The Stylish Dress Watch: Martenero Kerrison Watch, $595 — Both rugged and yet refined, this is the stylish leather watch to wear to Thanksgiving (and any holiday party, for that matter). Not too loud, not too subtle — Martenero has done things “just right” here.
  • The Grooming Essential: Lumin Moisturizing Balm, $29 — For a big holiday like Thanksgiving, you’ll want to look your best — clear, refreshed skin is a crucial part of that. With that in mind, Lumin’s Moisturizing Balm (as tested by yours truly recently) is some of the best on the market.
  • The Travel Bag: WP Standard Canvas Travel Bag, $298 — The best bag to pack for Thanksgiving? Very nearly. WP Standard comes through with a dependable travel bag that’s perfect for a long weekend.
  • The Host Gift: Cooper and Thief Bourbon Barrel-Aged Red Wine, Price Varies — If you’re able to check a bag or bring along a gift for your host, reach for a richly crafted bottle of red wine aged in bourbon barrels. It’s absolutely perfect for the holiday season.

Again, what’s the key in getting ready for a casual-yet-sharp Thanksgiving, the kind of holiday you can really enjoy in style? It starts with solid building blocks, including the perfect casual blazer for a bit of polished style. It works quite nicely when worn atop an American-made flannel for casual style that won’t quit — and again, that flannel is multi-faceted and versatile. It all comes together in terms of standout off-duty style thanks to slim denim from American menswear master Todd Snyder, as fitting a designer to wear on this holiday as any. Team it all with rugged-yet-sleek Chelsea boots for a sharp finish to the main components of this Thanksgiving outfit. Yet, we’re not done yet. Stay on time through your travels with the remarkably rugged Martenero watch shown above, and be sure to use Lumin’s Moisturizing Balm to freshen up your mug for the holiday. Naturally, Thanksgiving is all about travel — and with that being said, you need a dependable travel bag from WP Standard for the holiday weekend. Bring along some Cooper & Thief bourbon barrel-aged wine for your host, and you just might be the hero of Thanksgiving. And with that, I’ll send you out to finalize your outfit and travel plans — oh, and stay tuned for more Black Friday-centric content later this week. Thanks for reading — I’m very thankful!

Style Suggestion: What to Wear to Thanksgiving Dinner

Editor’s note: Surf The Style Guide for more menswear suggestions for every occasion.

Ladies and gentleman, Style Guide fans and first-time readers … drum roll please … presenting the fourth (yes, FOURTH) Thanksgiving day style suggestion on this blog! It’s pretty wild. And yes, I said the same thing last year when reflecting on past entries. After all, that’s what this holiday is all about, right? The chance to sit back, reflect and think on all the things for which we’re thankful. From friends and family to my career in New York City to this blog, I’m thankful every day for the chance to do what I love, and share it with great people. It’s definitely on my mind as I prep to travel to Florida for the holiday — and given the impending warm weather, my travel style looks a bit different than the suggestion below (if you’ll be in a warm climate yourself, give these warm-weather style tips a once-over). Whether your holiday takes you somewhere a bit more casual or somewhere that calls for dressing to the nines, I hope you’ll pick out useful pieces from the below — or the whole outfit, maybe? At any rate, follow along via Instagram and Twitter for more useful style tips. Stay warm, travel safe and enjoy the holiday in style. Thanks, as always, for reading!

The Sweater: JackThreads Bear Sweater — $64

A sweater with a bear on it? Sure thing.

A sweater with a bear on it? Sure thing.

Yes, folks — that’s a sweater with a bear on it. A bit whimsical and fashion-forward? Slightly. A fun way to nod to the holiday season with a bit of color? It’s that one, too. It’s a fun piece that isn’t for everyone — a slim cardigan would also do the trick — but it’s a way to channel throwback vibes that seem to be everywhere in recent years, from retro leather sneakers to well, printed graphic sweaters. You could always grab a stylish crewneck sweater — sans the print — if you’re so inclined.

The Shirt: Taylor Stitch Everyday Chambray Shirt — $118

Taylor Stitch

It just doesn’t get any better than the Everyday Chambray Shirt from Taylor Stitch.

From transitional fall style to a weekend coffee date and nearly everywhere in between, the Taylor Stitch Everyday Chambray Shirt has your back — and then some.  It’s a true four-season shirt made with a 7oz. Japanese chambray that’s durable but not overly heavy. In short, it’s ideal for layering under that nifty sweater — or wearing on its own with the sleeves rolled up if you happen to be in a warmer location. The folks at Taylor Stitch get plenty of things right, and this much-loved slim chambray shirt is perfect for the holiday season — or really, any time of year.

The Pants: Flint & Tinder 365 Khaki Pant — $98

The ideal in-between option for Thanksgiving -- crisp enough to go dressy, casual enough to with a chambray shirt.

The ideal in-between option for Thanksgiving — crisp enough to go dressy, casual enough to with a chambray shirt.

Now, the 365 Khaki Pant from Flint & Tinder has proven to be a hot seller in recent weeks, so you might be better off snagging slim chinos from the likes of Bonobos. Heck, even a pair of Flint & Tinder denim might work in a pinch if you decide to go a bit more casual with your look. But if you do stick with the 365 Khaki Pant, you’re getting a classic five-pocket pant with quality construction and the sort of versatile style that works as well on Thanksgiving as it does during a spring Friday with your favorite pocket tee — that versatility is worth the price tag, and then some.

The Boots: Johnston & Murphy Karnes Captoe Boots — $198

A durable lug sole blended with a handsome tan color and a functional wool collar.

A durable lug sole blended with a handsome tan color and a functional wool collar.

Assuming you live in a state where it might be just a tad bit chilly or snowy, sturdy, stylish leather boots are going to be your best bet for fighting the weather and looking great.  With a comfortable and functional wool collar, sharp detailing across the toe and a rich tan color, the Karnes is the perfect complement to a rugged chambray shirt and slim five-pocket pants. They’re refined, yet still able to stand up ably to any foul weather — and the price ain’t half-bad, either.

The Watch: Armogan Spirit of St. Louis Chronograph — $194.98

Vintage numerals blended with triple chronograph functionality in a handsome package.

Vintage numerals blended with triple chronograph functionality in a handsome package.

When you need accessories that find that tricky middle ground between casual and dressed-up, where to turn? Well, Huckberry  has you covered — at least when it comes to the Armogan Spirit of St. Louis Chronograph. With a vintage-inspired dial inspired by the single-engine plane piloted by Charles Lindbergh, it’s a handsome conversation starter (and it’s not related to politics or your dating life, either). The triple chronograph movement adds functionality to a crisp white dial — and the whole thing will look great every other day of the year, too.

A straightforward casual leather belt with fall-ready texture.

A straightforward casual leather belt with fall-ready texture.

If you’re spending some extra coin on a slim chambray shirt and a stylish casual watch, there are ways to cut back your spending a bit elsewhere. An easygoing casual belt from J. Crew Factory is step one in that regard — you’re getting a braided leather belt with seasonally appropriate texture, one that strikes the right tone with the casual-rugged vibes of this ensemble. Ya dig? Good.
Textured cotton socks that complement the rest of this outfit ever so slightly.

Textured cotton socks that complement the rest of this outfit ever so slightly.

You didn’t think we forgot about socks, did you? The difference is in small style details, and whether you keep your shoes on in your own home or someone else’s, a pair of well-made comfortable socks are a nice thing to have in your top drawer. Seriously, no one wants to have ratty socks as you walk to get that turkey sandwich — right? American Trench makes some of the best pairs in the game, and these pair perfectly with the cream sweater, blue shirt and khaki pants.
The Hat: Carhartt WIP Key Ribbed Beanie, $35 (Available via East Dane)
Simple, stylish and effective -- everything a good beanie should be.

Simple, stylish and effective — everything a good beanie should be.

This particular beanie has come up before from the good folks at Carhartt WIP. The brand makes pieces that merge functionality and a slightly fashion-forward approach, but this simple ribbed navy beanie is as straightforward as it gets. Particularly if you get outside for a game of backyard football, you’ll want a beanie that can keep you warm and work with the rest of your outfit — no athletic logos in sight on this thing.

Beckett Simonon

The above #menswear ensemble goes to show you that great style can go a long way, even when spending the day surrounded by family and friends — possibly in your own home. Starting with classic, essential basics — like a stylish chambray shirt and khaki pants — allows you to have a bit of fun with a printed sweater. And when chilly weather comes calling, rugged-refined leather boots a navy beanie are just the ticket in terms of versatile, functional style. Plus, the Spirit of St. Louis Chronograph can work just as well for your 9-to-5 grind as it can when spending time with family and friends. How will you be enjoying the holiday? Chime in over on The Style Guide Facebook page when you get the chance.

And of course, know that I’m thankful for all of you who read this blog — we’ve got more menswear in store this week, that’s for sure!

-Beau