#OOTD: How to Dress for a Fall Road Trip Right Now

We’ve been talking for some time now on the blog about how to dress for early fall (and beyond), and now that we’ve officially crossed over into the season itself, let’s pivot ever so slightly. Let’s go beyond the confines of your home office and your back patio, and let’s talk about how to dress for a fall road trip. I’m not talking about hopping on a cross-country flight — I’m moreso talking about the kind of trip where you pack up a durable duffle bag, grab your most rugged denim jacket, bring along your craft beer growler … and then get in the car and go. Where to?  A cabin, the lake, the river, a quiet town upstate … any and all of the above, right? Right. What to bring with you?

Well, a stylish face mask, for starters. But beyond that, we’ll cover all your fall style essentials for a road trip today on the blog — rest assured of that. Comfort, durability and style are the key here, seeing as you might be going off-trail for a hike or spending plenty of time on your feet, hopping from brewery to brewery (patios and masks preferred). Given that approach, you’ll find the best pants for fall travel and some stylish sneaker boots in the mix, too. Of course, all the right layers are along for the ride, including a tough workwear shirt  and a rugged leather watch. These are picks suited for casual (masked) strolls around town, and with a bit of improvisation, you can get out the door for that orchard or winery tour (at least, that’s what I’d do). How about it? Is this #OOTD ready for fall? I sure hope you think so. Stay safe, gear up and let me know what you think of this ensemble on Twitter.

Versatile, rugged layers for hitting the road this fall.

  • The Jacket: Todd Snyder Japanese Stretch Selvedge Denim Jacket, $288 — Made from rich indigo Japanese cotton with plenty of stretch, this classic denim jacket is one of the best denim jackets around, and it’s ideal for falll layering given the built-in stretch.
  • The Shirt: Flint and Tinder Selvage Architects Shirt, $128 — Layer up your rugged denim jacket with a new Flint and Tinder shirt, cut like a classic Oxford shirt and yet featuring Japanese selvage fabric for tough durability in fall weather.
  • The Tee: Buck Mason Long-Sleeve Raglan Tee, $52 — Keep the fall layering rolling with one of the most comfortable long-sleeve tees around. Buck Mason gets it done.
  • The Pants: Western Rise AT Slim Pants in Sand, $128 — Cut in a classic five-pocket silhouette and featuring plenty of durability and stretch, these Western Rise pants are the best pants for fall travel, period.
  • The Sneaker Boots: HELM Cole Sneakers in Wheat, $240 — The brand that makes some of your favorite boots (as seen here) is now making some of the best men’s sneakers, cut to be the perfect hybrid between, well, sneakers and boots.
  • The Watch: Luminox Atacama Field Chronograph, $940 — If you want a rugged leather watch that you can wear on the road and then out to grab socially distanced craft beers, you want this durable field watch from Luminox, my friends.
  • The Hat: Huckberry Explorer’s Cap, $40 — A fittingly named hat for fall adventures, and certainly one of the best men’s ballcaps out there.
  • The Travel Bag: Halfday Garment Duffle, $95 — Looking for the best travel bag under $100? You’ve found it. This garment bag from Bespoke Post zips into a stylish duffle bag, and comes complete with tough hardware, a built-in shoe compartment and more.

If I had to guess, I’d wager that this #OOTD is going to carry you through fall more than stylishly and reliably, no doubt about it. If you’ve been wondering how to dress for fall, period, or how to dress for a fall road trip, start here. A rugged workwear shirt teams stylishly with your new favorite denim jacket, and of course, that combination layers up more than readily with one of the best long-sleeve T-shirts for fall, courtesy of our pals at Buck Mason. When it gets a bit too warm (as is known to happen with shifting winds and fall sunlight), ditch the denim jacket and stick with the long-sleeve tee and your Flint and Tinder shirt. It all works in harmony with the best pants for fall travel, a durable pair that’ll stand up to fall weather and long hours in the car. But of course, a pair of the best men’s sneakers takes the cake on the footwear front (make sure your HELM boots are packed in your bag, of course) — there’s nothing better than comfortable sneaker boots for the trail and the taproom, am I right?

It all comes together in precisely the right way on the accessories front when you consider the versatility of your durable field watch from Luminox, fit for all-day wear. To keep the sun off your face and shield your eyes from the wind ever so slightly, throw on the Huckberry Explorer’s Cap for anything and everything on your to-do list. Last but certainly not least, a versatile duffle bag is the perfect way to haul your weekend style essentials (and it’s easy to pack and easy to zip out into a hanging garment bag). Alright, folks. Who’s ready to hit the road? I’ll see you out there. To get the scoop on how I’m dressing for fall, head to my Instagram

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