The List: These are the Best Men’s Gear Picks to Start off October the Right Way

The best casual sweater for a fall weekend? I’ll let you be the judge of that.

So, join me for another edition of The List — and this one, the first one of October, is all about ever-critical, versatile fall layers. The time for fun and games is over (well, in a way) — you’ve had some Oktoberfest beers, you’ve attended a tailgate or two or three, and now, it’s time to keep gearing up for more fall fun. With a focus on rugged-yet-wearable picks like the Relwen Windzip Popover, I’m betting you’re going to layer up for fall with ease (and style) in mind. Of course, you’ll find plenty of complementary picks on the docket, including rugged flannel shirt from Taylor Stitch — that’s just the tip of the iceberg. Happy October, my friends.

Relwen Windzip Popover — $218

No wrong way to go with this durable popover sweater, guaranteed.

As discussed above, you’ll see we’re all about versatile fall layers this time around — after all, it’s in the air right now. That being said, the Relwen Windzip Popover is one of the best layers for fall, made to durably take you through tailgates and camping trips aplenty.

Timex x Todd Snyder Beekman Watch — $158

I’ll leave it up to you as to whether this is one of the best black leather watches on the market.

As far as the most affordable men’s watches go, the ongoing Timex x Todd Snyder collaboration has to take the cake. The Beekman Watch could just be the best black leather dress watch for men, and it’s well-suited for a fall wedding, too.

Filson Watch Cap — $45

A tough watch cap to wear into fall.

We’ll move from talking about a watch to wear to a fall wedding to the rugged beanie cap to wear in your downtime. Get on this affordable Filson beanie cap while there’s still time.

Faherty Brand Slub Cotton Henley — $98

An excellent men’s henley for every fall weekend.

Rest assured, this won’t be the last rugged henley we’ll talk about in today’s post — but it’s simply one of the best men’s henleys around, so it gets the nod here. Faherty Brand does a wonderful job using rich fall fabrics and excellent seasonal colors.

Flint and Tinder Flannel-Lined Waxed Trucker Jacket — $220 

The return of an old favorite via Flint and Tinder.

If you read the blog, you’ll recall the simply magnificient, perfectly rugged and (newly) iconic Flint and Tinder Flannel-Lined Trucker Jacket. Well, folks. It’s back. Layer up for fall accordingly.

Rancourt & Co. Court Classic 2.0 — $280

The best white leather sneakers are up for the taking as we move into fall.

Can you wear white sneakers into the fall? Yes, you can (white jeans are another story). But the best white sneakers can be worn plenty of days (and ways) during October, particularly when it’s warmer than expected. Rancourt & Co. does things the right way with this sleek leather pair.

Taylor Stitch Crater Shirt in Rust Plaid — $98 

One of the best flannel shirts you can pre-order at the moment — like, right now.

You’ve got just enough time to pre-fund this rugged flannel shirt from Taylor Stitch. The Crater Shirt is the kind of shirt you’re going to love to wear on fall weekends aplenty, particularly with classic raw denim from Mott and Bow — speaking of …

Mott and Bow Slim Oliver Raw Denim Jeans — $108 

Slim, deep blue denim to wear deep into fall from Mott and Bow.

Now, just because we talked above about the best white sneakers doesn’t mean we’re giving up on tried-and-true fall dressing entirely. Case in point: This rich, dark blue pair of classic raw denim from Mott and Bow. Perhaps the best men’s jeans to wear all fall.

Good + Well Supply Co. Sequoia National Park Candle — $36

A simple, subtle way to upgrade your home this fall.

As to be expected, scented candles for fall are all the rage right now — so don’t be surprised if this one is sold out. That being said, a candle is a perfectly simple way to upgrade your home, seeing as it’s inspired by an American treasure.

Howler Brothers Merlin Jacket —$199

Need a jacket that doesn’t quit when the going gets tough? Get this Howler Brothers jacket.

When it comes time to gear up for inclement fall weather — either as you tackle early morning yard work or gear up for an early morning tailgate — the tough Howler Brothers Merlin Jacket (as previously seen here on the blog) is one of the toughest fall jackets you can ask for, and it’s crafted from micro-ripstop, at that.

Astorflex Bootflex Boots — $195

These are the best new boots for fall, full-stop.

You’ll find plenty of gems when it comes to the best men’s boots for fall via Huckberry, but the Astorflex Bootflex Boots — perfectly rugged and casual all the same — are a must-have for your closet.

Flint and Tinder French Terry Pullover Hoodie — $69.98

The perfect weekend hoodie? Yes, it could be.

This stylish hooded sweatshirt — and others like it — have popped up across The Style Guide in recent weeks, and with good reason. This French Terry hoodie is premium and rugged, able to be worn atop your favorite T-shirt or alongside an Oxford shirt for the right blend of casual and laidback appeal. Team it up with those Astorflex Bootflex Boots, too.

Old Enfield Heritage Dopp Kit — $62.98

The perfect dopp kit for your favorite grooming essentials.

For fall travel, be it an upstate weekend getaway or a jaunt to a fall wedding, you need one of the best men’s dopp kits. It’s an understated accessory that pays big dividends, and the Old Enfield Heritage Dopp Kit checks all the right boxes.

Wellen Hemp Long-Sleeve Henley — $39.98 

The henley to wear all fall — and then some.

Finding an affordable long-sleeve henley can be tough — but in terms of sustainability and style, Wellen is unmatched. This is the rugged fall henley to wear all season.

Obermeyer Carson Down Vest — $129

A casual, cool, adventure-ready vest.

In the way of essential fall layers, it’s tough to go wrong with a rugged, insulated vest for fall — especially this retro-inspired, colorblocked number for fall.

Howler Brothers Howler Club Snapback — $30

A cool canvas cap for a fall weekend.

We’ll close out today’s roundup of the best men’s gear with a casual fall weekend cap, crafted with retro style and laidback sensibility in mind. Throw on this Howler Brothers cap (yes, more from that brand!) to grab some beers at your favorite bar.

Alright,  now mark my words … that was a HECK of a lot of classic fall gear to sort through, was it not? From the small essentials (like a casual fall weekend cap or a scented candle for fall) to the bigger purchases (see: The best black leather dress watch for men and the Flint and Tinder Flannel-Lined Trucker Jacket), I hope you found something you’ll enjoy. Have any particular favorites? Let me know on Twitter!

Online Shopping Picks: Grab This New Gear for Early Fall

What exactly do we mean at The Style Guide when we say early fall gear? That’s the question, right? Well, we’re on the verge of September and if you haven’t put together your fall style wish list, perhaps it’s time to start thinking. We’ll be focused on my fall style favorites next week, but for now, let’s get a jump on shopping — shall we?  We’re digging into those nice-to-have essentials for when that first crisp breeze hits and you head out to a football tailgate or a day hike or a bonfire … or any other like-minded fall pursuits. When the time comes, you’ll, be ready. A handsome leather flask? You got it.  A rugged leather dopp kit for all your long weekends away?  It’s on this list below.  There a few other picks that straddle the line between apparel and handy everyday carry gear, and that’s a good thing — fall is perhaps the best season for #menswear, right? With that spirit in mind, let’s get to work. After all, fall’s on the way. If you want to see how I’m transitioning into the season, hit the “Follow” button on Instagram, or keep up with my of-the-moment musings on Twitter.

The Boots: Unmarked Roll-Top Desert Boots — $159.98

Classic, uniquely made and ready for fall adventures.

What would fall be without a unique, yet decidedly classic, pair of desert boots? Particularly early fall, ehh? Unmarked is making its Roll Top Desert Boots with both craftsmanship and flair — these feature a unique silhouette, handmade construction and a one-piece heel counter/ankle collar. Construction details aside, they’re the ideal pair of rugged (yet not over-the-top) classic desert boots to take you into early fall.

The Sweater: Flint and Tinder 10-Year Pullover in Navy — $89

Flint and Tinder

The type of hoodie you can wear over a classic Oxford — seriously.

Just as you need an easygoing pair of desert boots for all occasions — or nearly all occasions — so too do you need a stylish sweatshirt that’s truly a grab-and-go piece. The 10-Year Pocket Pullover from my pals at Flint and Tinder features better looks than your average hoodie, thanks to raglan stitching and no gaudy logo. Add in the soft fabric, the on-point fit and the array of color options, and the 10-Year Pocket Pullover is  a sweater that can go from the apple orchard to the bar, no sweat.

Gear Patrol American Craft Beer Field Guide — $9

Gear Patrol Field Guides

A trusty guide to take with you on a weekend trip.

While we’re out there talking rugged menswear like a classic hooded sweater and stylish desert boots, let’s talk about travel companions. Like, for instance, that trusty book you take with you wherever you go, and can pick up just about any time. The first of many Gear Patrol Field Guides fills that void if you happen to be a craft beer lover  (like me). And seeing as fall is a prime time for switching from light, crisp beers to richer brews, you best study up. Perfect for taking on a weekend away, preferably en route to a brewery.

The Flask: Slightly Alabama Hand-Stitched Leather Flask — $109.98

Ever seen a flask this cool? I certainly haven’t.

Ahh, here it is: The handcrafted, rugged leather flask we mentioned earlier. It’s the small pleasures in life that really count, and if ever you’ve wanted to take your favorite spirit to a tailgate or bonfire in style, this Slightly Alabama leather flask is the way to do it. With plenty of attention to detail and an aesthetic that doesn’t look half-bad resting on your mantle, Slightly Alabama has outdone themselves here — an expensive piece, but well worth it.

The Bonfire Essential: Sturdy Brothers Firewood Carry — $127

A heck of a way to haul your firewood — to say the least.

OK, maybe it’s not a full-on essential if you’re a city dweller like yours truly. And yet if you dwell outside the big city, why not grab something that’s rugged, durable and tough as nails to haul that firewood you’ll undoubtedly be chopping for bonfires aplenty? Again, do you need the Sturdy Brothers Firewood Carry? Ehh … perhaps  not. But will the Sturdy Brothers Firewood Carry work for seasons to come, through all types of weather? Absolutely.

The Travel Essential: Sturdy Brothers Horween Leather Dopp Kit — $138

Make this dopp kit the next addition to your weekender bag, yes?

OK, you’ve got your handy field guide, your rugged desert boots and your stylish weekender for an early fall getaway. What are you going to put your toiletries in for said getaway? Easy: The Sturdy Brothers Horween Leather Dopp Kit. Certainly, it’s a unique choice as far as dopp kits go, but the rugged leather and standout color of this stylish dopp kit will definitely help it fit in with the cooler climes of fall. It’s all about the details, yes?

We’re going to wrap this one up now — time to prep for fall, ehh? Transitioning from the heat of summer is all about reaching for pieces that are suited for all your fall adventures. Take rugged desert boots and a stylish casual sweater and wear ’em through plenty of weekends, for starts. And those everyday carry pieces that you can’t go on a trip without — like a uniquely stylish dopp kit — are going to serve you well, too. And then … because it’s fall … there are tough-as-nails pieces of gear that are just pleasing to have around. Take the Slightly Alabama leather flask as seen above, or the rough-and-ready Sturdy Brothers Firewood Carry.  After diving into this post, I’m certainly ready for a little early fall fun. How about you? You can check back here next week for our full Fall Style Wish List. Up next: A new See Now, Buy Now  post! 

Stay stylish!