#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

#OOTD: Wear This Gear to Layer Up on A Chilly Fall Morning

When you feel it in the air, you just know. That is to say, the sort of cool, crisp fall morning that calls out to be enjoyed with your favorite fall gear picks and a hot cup of coffee in hand as the mist rolls in — that’s quite the idllyic picture to paint, and maybe your weekend morning view looks a bit different (it does for me in Brooklyn!), but the best fall style essentials for a casual weekend can help you gear up any which way you slice it. So today, we’re going with the kind of cozy, casual gear that’ll work well for a weekend coffee date or a cool, laidback morning in equal measure — think of the rugged layers that a menswear hero like Daniel Craig wears in “The Girl with the Dragon Tattoo,” for instance. That is to say, a rugged sweater from Wellen in a fittingly thick knit should wear mighty nicely with a classic chambray shirt for when it’s too cold to do anything but bundle up more. And the rest of these picks are able to go into town or host guests at home, too — take slim faded black jeans and pair them up with classic leather hiking boots to get a dose of functionality and style all at once. Of course, we’ve also got a cozy merino beanie and a tough leather watch standing tall on the accessories front. All you need for the morning is a great cup of coffee, and then in the evening, kick back with a sip of whiskey. This rugged #OOTD will do the rest. Cheers to fall!

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Rugged fall style made easy with casually laidback (yet versatile!) picks.

  • The Sweater: Wellen Headlands Sweater, $138 — Again, we’re going for the sort of rugged vibes you can only conjure on a chilly fall morning. This classic, vintage sweater from Wellen gets it exactly right.
  • The Rugged Fall Shirt: Buffalo Jackson Harbor Chambray Shirt, $55 — Any old shirt simply won’t do. This rugged chambray shirt is perfect to throw on without overthiking it, wouldn’t you agree?
  • The Denim: Flint and Tinder Stretch Selvage Jeans, $168 — There’s a difference between throwing on sweatpants (as stylish as they might be!) and then throwing on these slim selvage jeans. Flint and Tinder knows this, and gets it right.
  • The Boots: Hanwag Bergler Boots, $400 — The key here is upgrading your rugged style essentials, starting with your new favorite pair of leather boots for plenty of consisten fall wear. Some of the best hiking boots you can buy right now, in fact.
  • The Watch: VAER Watches Heritage Watch, $209 — This VAER Watches timepiece might just be the best casual watch to wear with this outfit — perfectly rugged in every way.
  • The Fall Hat: Hill City Merino Cashmere Beanie, $48 — Pick up this exceedingly comfortable, cozy fall beanie cap to throw on for all your weekend errands — style points guaranteed.
  • The Grooming Must-Have Guru Nanda Charcoal Toothpaste, $19.99 — Get a great deal on a six-pack of whitening toothpaste made with high-quality, functional charcoal and peppermint — your smile just got that much brighter.
  • The Essential: Jumper Boxer Briefs, $25 — The little details, as we all know, make all the difference. And when it comes to the best boxer briefs on the market, Jumper easily takes care of business with solid, reliable basics.Shop Mott & Bow Today!

Oftentimes, you needn’t overthink what to wear on a  chilly fall morning or evening. In this instance, a vintage sweater from Wellen does the heavy lifting in terms of comfort and style, and it pairs up very well with arugged chambray shirt for style that’s effective, warm and laidback — all at once. To really solidfy the balance between casual, rugged and versatile, step out with a pair of slim selvage jeans, too. That is to say, this is the kind of look that can work nicely for a laidback morning or afternoon in town just as well as it can during an evening cocktail in front of the fire. Of course, should you need to get out and about, your new favorite pair of leather boots are more than ready to take on fall and winter weather. The accessories shown here also should get the job done, no matter what — take, for instance, the subtle style you get from wearing perhaps the best casual watch — it’s a surefire way to stand out quietly no matter the occasion. A merino beanie, comfortable boxer briefs and surprisingly effective charcoal toothpaste are all small details that make a big difference, too. When you take this outfit in total, I’d say it’s as ready for fall adventures as you are. In the meantime, follow along on my Instagram to see how I’m dressing for the season.

 

#OOTD: How to Dress for Early Fall This Year

If it makes you jump out of your seat a bit to see the words “early fall” in a headline, know that I’m every bit as surprised by the end of summer as you. In that regard, we’ve been telling you all about the men’s style essentials to get you ready for the next season across these past few weeks, and today is no different. Our #OOTD focuses on the kind of gear you’re going to want to start slowly incorporating into your fall lineup, from a vintage-inspired chambray shirt to rugged leather boots and, simply put, the perfect pants to wear for early fall. This season is all about gear that can work with you in multiple situations. That’s why (as you’ll see), we’re incorporating a heavyweight pocket tee from our pals at Filson into the mix, seeing as you can wear it on its own during the day to grab a weekend coffee, then layer it up at night to grab cocktails at that new speakeasy in town. We’re also including a tough bag for your everyday carry, not to mention one of the best men’s watches you’ll find anywhere. Jumping into fall doesn’t have to be something you do all at once — mixing and matching the kinds of pieces that work in multiple seasons (and style situations!) is the way to go. So, ideally, this post can help you start to leave summer in the rearview mirror (sadly!) and look toward a crisp, cool, fun fall. Have questions for me on fall style tips? Reach out on Twitter.

 

Pairing a classic chambray shirt with a classic summer T-shirt — and classic leather boots. Get the idea?

  • The Shirt: Dickies 1922 Chambray Shirt, $190 — To be sure, we’ve been recommending pieces like a classic chambray shirt a lot lately — it’s the perfect layer to take you into the early part of next month, and this Dickies 1922 shirt is based on an old archival style. Utterly classic.
  • The T-shirt: Filson 8oz. Solid Pocket Tee, $55 — Leave it to Filson to craft a timeless pocket tee in a substantial fabric, perfect to wear on its own or layer underneath your new favorite shirt.
  • The Pants: Proof Rover Pants, $98 — A fitting hybrid between chinos and jeans is what this time of year calls for, and these might be the perfect pants to wear for early fall (and beyond). Easy to move around in, extremely breathable & also well-made.
  • The Boots: Red Wing Heritage Rover Boots, $269.99 — The key to moving this outfit from summer into early fall? Rugged leather boots from Red Wing Heritage, the kind that are still lightweight and versatile enough to wear with the Proof Rover Pants.
  • The Watch: Lum-Tec M84 Automatic Watch, $1,095 — Yes, we’ve been featuring this rugged Lum-Tec watch a fair amount on the blog as of late, all owing to the fact that it’s simply one of the best men’s watches on the market, and perfect for this outfit.
  • The Belt: Arcade Belt Co. Norrland Woven Belt, $38 — Finding a functional, rugged belt is no small task, but Arcade Belt Co. comes through with one of the best men’s belts we’ve seen — this is no flimsy, thin leather belt that you’d pick up by the check-out rack at a fast-fashion shop, mind you.
  • The Everyday Brief: Boarding Pass NYC Flight Brief, $199 — Thinking about taking this show on the road? Even if it’s just to knock out some work at your local coffee shop, this rugged, durable & yet refined flight brief is perfect for your everyday carry.
  • The Grooming Essential: West Skincare Recovery Cream, $55 — If you’re not yet acquainted with West Skincare, consider this your introduction. This is active skincare made for guys who need active recovery, and this cream in particular is designed to hydrate and restore skin.

Now, if you’re not feeling ready for early fall yet, well, consider this a helpful guide to get started. When you start out wearing a classic chambray shirt, especially the rugged Dickies vintage shirt above, you’re setting yourself up for success — it’s perfectly casual and versatile enough for summer and fall. The same can be said of the equally rugged Filson pocket tee, again the type of tee you can wear all on its own or under any shirt you’d like. Throw in quite possibly the perfect pants to wear for early fall, and you’ve got a winning base for an outfit that’s geared to sip on an Old Fashioned, crack open a cold beer or visit your local park. In fact, that’s where rugged leather boots from Red Wing Heritage can come in mighty handy — they’re extremely tough & versatile enough for multiple seasons. And when you accessorize with a rugged Lum-Tec watch, you’re keeping the outfit squarely in casual, go-anywhere territory. The only thing to do now? Grab your Boarding Pass NYC flight brief, accessorize with a functional, rugged belt and your everyday carry, then finish off your look with West Skincare’s Active Recovery Cream. OK, now who’s ready for early fall?

The Friday Read: Rugged Fall Style, Oliver Cabell and Hard Graft Gym Bags

Editor’s note: Expect these posts once a week on Fridays — consider this a jumpstart on reading for your weekend downtime. Expect a mix of style and non-style content. For more entries, click here.

So if you’re joining us here today on The Style Guide, that must mean it’s Friday. And if it’s Friday, it’s time for another round of The Friday Read, where we tackle the best of the week in #menswear — with a dash of music and fine spirits joining us in today’s post. First things first — thanks to everyone who participated in this week’s Dickies X-Series Denim giveaway this week. We’ve had the pleasure of some crisp, brisk fall weather this week in NYC — if that happens to be the case for you as well, I’d urge you follow the behind-the-scenes action on Instagram and check out how to dress for fall. We’re talking indigo chore coats, slim garment-dyed pants and a tough Horween leather watch. Oh, and an essential crewneck sweater for your fall wardrobe — that’s a thing, too. It’s been fun to break out some tougher layering pieces for the chilly weather, and rest assured that we’ve got plenty more fall style-centric content in the weeks ahead. Namely, we’re diving into the archives with tomorrow’s Style Pick of the Week — and then jumping right back to the present day with our very own Thanksgiving Style Suggestion. It’s tough to believe it’s that time of year already! But, not to worry — we’ll be offering up all manner of holiday style picks, from what to wear to your holiday party to what to buy for your significant other. In the meantime though, I’ve got a weekend of travel ahead — I’m heading on a quick trip upstate to the lovely town of Hudson for a bit of rest, relaxation and menswear-themed exploration. Follow along via Twitter, look for a full recap blog post coming on Monday, and check out everything you need to know from the week in men’s style news.

  • Who can pass up the chance to combine refined spirits and great menswear? Not that many folks, that’s who. The fine spirits purveyors at Glenfiddich launched a fall capsule collection — titled Wardrobe XXI — with none other than menswear luminary Josh Peskowitz. The lauded fashion vet, who recently opened up Magasin, a menswear lifestyle boutique, curated four men’s style capsule collections on behalf of Glenfiddich. The brands run the gamut from contemporary — Camoshita United Arrows to slightly edgy (FEIT). And each capsule, which is sold at select retailers like NYC’s Gentry and Miami’s Alchemist, pays homage to Glenfiddich’s 21 Year Old Reserva Rum Cask Finish. Now, great whiskey and great menswear? That’s something we can all get behind.
  • If you’re hitting the road for Thanksgiving next week, you need to know how to travel in style. That just got easier with the introduction of the Arcata Travel Kit from premium accessories brand Oliver Cabell. We rounded up the best dopp kits for men on this blog earlier this year, but this dopp kit is a worthy addition. Thanks to the brand’s transparency — right down to the material and labor costs displayed on its Web site — you know you’re getting a premium, road-ready piece.
  • We’ve covered the best men’s weekender bags, but you might want to add another to your list. The Hard Graft Gym Bag Volume Two is a beautifully crafted, superbly done bag that merges tremendous functionality with stellar looks. Give it a read via yours truly at GearMoose!


Looking for something to read — or listen to — this weekend?

  • If it’s a relaxing weekend listen you seek, might I suggest the eloquently produced “On Hold” from everyone’s favorite ethereal music trio, The xx? Give it a listen over at Pitchfork. You won’t regret it!

That’s all we’ve got from my neck of the woods — stick around and check out your new favorite fall jacket, or a rugged fall layering essential, before you take off for the weekend.

Stay stylish,

-Beau