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.
- 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!