The Friday Read: The Best Stores Like Zara, New Menswear from Todd Snyder & Fall’s Best Boots

Todd Snyder Fall 2021: 15 Can't-Miss Buys From the Latest Drop | GQ

It’s hard to believe, seeing as I just talked about the best discounts on menswear at Todd Snyder last weekend, but it’s already time to start thinking about the best fall menswear from the lauded designer (and plenty others, of course). Labor Day is right around the corner, and you’d do well to outfit yourself in some of the coolest transitional outerwear, lightweight, easy-to-layer sweaters and expertly faded jeans, among the latest and greatest from the Todd Snyder Pre- Fall Collection. The choice is yours (and you can also find plenty of fall style staples at my Shop By The Style Guide), but Todd Snyder menswear is one heck of a place to start.

Stock up for fall with Todd Snyder menswear

Layer up with premium men’s style essentials

I’ve got new fall gear on my mind this week, even as I close out a family vacation in Michigan (I’ll cover my trip a bit more in my weekend newsletter) — I’ll be back in NYC in early September, and ready to ring in the season, as it were, with rugged henleys, waxed jackets and more. You can check out all my favorites for the season ahead, once again, at my Shop By The Style Guide , but you should also keep an eye on my writing at sites like AskMen, where I’m also covering plenty of seasonal style staples. But enough about fall. Right now, I’ve got some sun to catch in Michigan this weekend. And the rest of your Friday Read? You can find it all below, folks.

  • If you read the blog earlier this week, then you’re hopefully well-acquainted with the boots shown above. If not, well, it’s never too late (or too early) to start shopping for the best men’s boots. Head over to Bespoke Post — after reading my blog entry, that is — to shop the most rugged men’s boots for fall from Red Wing Heritage. It’s really that simple.

Get the Red Wing Iron Ranger Boots now

Lace ’em up for fall this instant
  • Let’s shift gears quickly to your home, and the goods within that home. It’s about time you invested in the best, is it not? That’s where Shinola’s partnership with Crate & Barrel comes into play. It’s part of the just-launched effort from the Detroit watchmaker to open its own home goods store and expand upon its current line of stylish desk accessories, record players and more — naturally, I wrote about my favorite Shinola For Crate & Barrel pieces over at Maxim this week. Happy shopping!
  • The headline mentions that I’ll be talking about the best stores like Zara, and that’s precisely what I’m doing here by way of my latest Effortless Gent feature covering the top alternatives to Zara. It’s long been an affordable bastion of high-fashion style, and it’s an ideal place to go if you want everything from a camel topcoat to slim denim in your rotation for the season ahead. Head to Effortless Gent — a site for which I’ve been writing for eight years! — to check it out.

Hopefully, a few of those picks have you thinking about how best to dress and accessorize for fall. I’m getting ready slowly but surely for the season ahead, and it’s with that approach in mind that I’m recommending you stock up on the best transitional outerwear, like this Flint and Tinder indigo trucker jacket that I covered here on the blog earlier this week. Again, it’s never too early to get ready for what lies ahead. Stay stylish and thanks for reading!

The Thursday Buy: The Red Wing Iron Ranger Boots are the Perfect Boots for Fall

We’ve talked a bit lately about how to dress in style for early fall, but the biggest key before you can actually get dressed is, well, stocking your wardrobe with the right pieces. Take, for instance, some of the best men’s boots for fall, the iconic, instantly recognizable and seriously rugged Red Wing Iron Ranger Boots. Since you’re shopping for the season just a bit early, you’re in luck: You can get your new favorite leather boots right now from Bespoke Post, with a solid selection of sizes and colors available. For me this year, it’s all about the durable and eye-catching Red Wing Iron Ranger Boots in Charcoal, a slight change of pace from other Red Wing Heritage Iron Ranger Boots (take, for instance, the Red Wing Iron Ranger Boots in Amber). Of course, I’ve certainly sung the praises of the Red Wing Heritage Iron Ranger Boots here on the blog over the years, but it’s always worth getting a refresher on a classic.

The rich Charcoal color is every bit as versatile and attention-grabbing as other men’s boots up for grabs right now, but it’s got a little something extra going for it. It’s the kind of pair of boots you can wear with a suit (preferably, in a fall fabric like herringbone or wool), but they’ll also be able to put in double-time when teamed with your favorite pair of blue jeans. And because these are Red Wing boots we’re talking about here, the appeal only builds from there.

SHOP: The Red Wing Iron Ranger Boots

Straightforward, dependable and hard-wearing has always been the name of the game with the Red Wing Iron Ranger Boots, which remain classic and stylish almost without fail. The original version, after all, was designed for iron miners in the 1930s, and Red Wing has stayed true to that commitment to quality and integrity. When it comes down to it, you likely won’t find a tougher pair of work boots (or boots for casually rugged style) than a pair of Red Wing boots. They’re also water and stain-resistant and of course, they’re made in the U.S.A.

Wear them with tan chinos and a white Oxford shirt for classic high-low style, or break them out with slim blue jeans and a pocket tee. When it gets colder, I’d wager you already know how to wear your Red Wing Iron Ranger Boots: Start with, say, a long-sleeve thermal henley and an indigo denim jacket, then consider adding a classic crewneck sweatshirt to the mix as it gets chilly. No matter how you choose to wear ’em, the Red Wing Iron Ranger Boots will come through in the clutch, every time you need an expert blend of style and durability.

SHOP: The Red Wing Iron Ranger Boots

The Friday Read: A Red Wing Boots Giveaway, New Mott and Bow Denim & Tom Brady’s New Sunglasses

Men's Classic Moc 6-Inch Boot in Brown Leather 1907 | Red Wing Shoes

An iconic pair of classic Red Wing boots, and just one of the many covetable pairs on offer from the brand this season.

My friends, it’s time you stepped into fall with a pair of Red Wing moc toe boots (available via UNCRATE) — like the rugged leather boots shown above, in fact. I’ve got some even better news, though. You’ve got a chance to win your own pair of archival Red Wing Heritage boots right now. The legendary footwear company is opening the Red Wing vault this fall, releasing a limited vintage footwear offering each month — one pair per month, with some styles dating back to 1963. Simply head to the brand’s Instagram page to find out more. And if, in addition to trying your luck, you’d also like to buy some Red Wing boots right now, you can snag ’em at retailers like UNCRATE in the meantime. Alright, now that we’ve stepped on into the weekend a little bit, who’s ready to get down to business?

There’s plenty to get excited about in the world of men’s style as we get ever closer to fall. To help you prepare for the season ahead, I’ve started writing for Huckberry’s revamped Journal — it’s back and better than ever, and I’m so pleased to be able to cover the best waxed trucker jackets and plenty more along the way. I’ve also kept plenty busy contributing to to start fall — more on that below, too! And before I put on another pot of coffee and start to scheme my next brewery visit (likely to Brooklyn’s Threes Brewing!), I’ve also got to shout that you can (and should!) hit Subscribe to get my newsletter, The Style Guide In Brief, delivered twice-weekly to your inbox — every Tuesday and Saturday, in fact. I’m talking indie rock, craft beer, the best fall gear and much, much more. How about it? Of course, you can also swing back through the blog tomorrow to check out my Style Pick of the Week. The rest of your Friday Read awaits below.

Men's - Faherty Brand

The best way to prep for the season ahead? Gear up with Faherty Brand, folks.

American Giant Hoodie Review -

  • Here we are with more of the best gear for a fall weekend. In fact, it comes from a brand you probably recognize from the blog: That, my friends, would be the good folks at American Giant. With a focus on casual, rugged men’s basics — including the best hooded sweatshirt for fall — the American Giant team is on the case when it comes to outfitting you in easy-going yet cool style for the season ahead. After all, when you put in the hours and focus on American-made menswear, the results are going to speak for themselves. Note that the brand has also shifted production to make some of the best face masks on the market during these trying times, too.
  • As I mentioned above, I’ve certainly stayed plenty busy on the writing front, including a recent feature for that’s definitely a highlight of my writing career. I caught up with NFL legend Tom Brady to talk all about his new eyewear collaboration with Danish brand Christopher Cloos! The partnership features plenty of stylish sunglasses and Blue Light eyeglasses, too. Read more before you snap up a (surprisingly affordable!) pair.

Well, how about it? Are you ready for the weekend — and ready to stock up on the best men’s gear for fall, no less? I certainly know I am. In the spirit of always being ready for what lies ahead, I’m going to point you toward my 25 best men’s gear picks for fall, an extensive offering (if I do say so myself) that really does have something for everyone. To wit: I cover everything from stylish leather boots to American-made socks, classic Persol sunglasses Filson Dry Tin 5-Pocket Pants and much, much more. Sounds too good to pass up, does it not? My friends, thank you for reading, thank you for being here & let’s start the weekend off right.


See Now, Buy Now: The Red Wing Heritage Wacouta Boots Are the Best Winter Boots

Durable boots that pack a punch in terms of winter style.

As we always say here at The Style Guide, it’s high praise to call out a pair of men’s boots as, well, the best winter boots — but if you stick around for today’s See Now, Buy Now entry, I think you’ll start to grasp why. And the  boots in question today have plenty of moxy to back up those claims: Yes indeed, the Red Wing Heritage Wacouta Boots are tough-as-nails, durable as can be, and supremely stylish to boot: Hence, the title of “best men’s boots” today. Coming right out of the gate, if you know the Red Wing Heritage brand, you’re aware that they continually go to great lengths to craft the best leather boots on the planet — the Wacouta Boots are no different. The use of tough full-grain leather ensures these rugged Red Wing Heritage boots can take a beating right off the bat, while other design touches (right on down to the classic Red Wing leather laces) only add to that durability.

SHOP: The Red Wing Heritage Wacouta Boots

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Also available in Briar Oil Slick leather with olive green waxed canvas.

What else makes these classic leather boots so essential? Friend, I’m glad you asked. These remarkable, rugged leather boots feature tough American waxed canvas accents for an added touch of durability and visual interest — seriously, just picture the Red Wing Heritage Wacouta Boots peeking out from beneath a pair of your favorite dark blue denim or better yet, some tough five-pocket pants (chambray shirt and classic peacoat not included). The even better part? The Red Wing Heritage Wacouta Boots are going to be able to pull weekend duty (heading to your favorite brewery and teamed with a shawl cardigan) or time at the office (again, add in classic five-pocket pants and a navy herringbone blazer). When Red Wing Heritage is in the mix, you can rest assured the results will deliver.

SHOP: The Red Wing Heritage Wacouta Boots


The Friday Read: Red Wing Heritage, the New Madewell Men’s Line & A Boston Weekend

It’s high time you laced up some of fall’s best boots for a great weekend.

It’s sometimes shocking how on-the-nose a product title can be when looking at the best fall gear for men — for example, the Red Wing Heritage Weekender Chukka, as shown above, should be on your feet for each and every fall weekend adventure you can dream up. They’re simply some of the best leather chukka boots you can get for your hard-earned cash, and if I was you, I’d make a point to snap them right up. That being said, they’re the kind of boots I’d pick up for a fall adventure of my own … kind of like the one I’m on as we speak! We’re coming to you from the lovely, fall-friendly confines of Boston, where I trekked last afternoon on a mid-fall getaway … complete with a rock show by my heroes, The National! I’ve been able to make it a point and a priority to crisscross the country (and the globe!) to see them on an incredible tour behind their latest album, “I Am Easy To Find” — these shows have been nothing short of lifechanging, from Nashville to Montreal across the pond to Madrid (and back to Brooklyn’s Prospect Park, of course). Last night’s show at Boston University’s Agganis Arena was nothing short of incredible either, including a banner run of cuts off of “I Am Easy To Find” — including fan favorite “Rylan” — and recent classics like “The System Only Dreams In Total Darkness.” At this point, I’d be hard-pressed to pass up any opportunity to see this world-beating band, especially if it only means a relatively quick train ride up the East Coast!

That being said, I’ve got plenty more on my Boston agenda as I set out to explore from the ecletic, modern FOUND Boston Common Hotel. I already had the chance to enjoy a delicious Old Fashoned pre-show at the seriously cool Deep Ellum near the Boston University campus, and my travels today will take me out on foot to spots like Trillium Brewing, fueled up by coffee from The Thinking Cup. I’ll also be checking out the menswear on tap at SAULT New England, naturally. Before I head back tomorrow, do you have any must-see spots I should hit? Let me know on Twitter! And in the meantime, let’s carry on with today’s roundup of essential weekly menswear news from yours truly.

OK, so that’s all I’ve got for you today. OK, well, not quite. Because a guy can never have too many pairs of stylish leather boots, I’m going to direct you back toward my post on the best chukka boots to buy for fall (a word to the wise: They’re coming at you courtesy of Huckberry and Rhodes Footwear). They’re so essential, so durable, so tough and yet versatile … they’ll become your new favorite pair of chukka boots, and I can nearly guarantee it. Now, if you’ll excuse me … I’ve got some Boston exploration to take care of! Enjoy your weekend, and thanks for reading.

See Now, Buy Now: The Red Wing Heritage Classic Chukkas Are the Perfect Winter Chukka Boots

Rough and tough chukka boots from an iconic branda.

Check your calendar. And now look at the boots you’ve got on. Are they a stylish pair of leather boots for winter? Better yet, are they the Red Wing Heritage Classic Chukkas? No and no? Well, let’s fix that today via the latest entry in our See Now, Buy Now series. Here at The Style Guide, your author loves a classic, iconic brand like Red Wing Heritage for reasons aplenty, chief among them being the brand’s ongoing commitment to timeless styles and seriously tough construction. Those are both qualities that are going to serve you well this winter. And the Red Wing Heritage Classic Chukkas in particualr just get the job done, to say the very least. Finding the right pair of winter boots is a tricky endeavor in more ways than one — you want a pair that can stand up to snow and slush, yet you’re also going to need to be able to wear them in a myriad number of style situations (as you dress for the office or head to your favorite brewery, in particular). Again, the Red Wing Heritage Classic Chukkas deliver.

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SHOP: The Red Wing Heritage Classic Chukkas via Bespoke Post 

Of note, they channel the same timeless construction and quality for which Red Wing Heritage is known, and the brand’s Minnesota roots sure do come in handy — the Red Wing Heritage Classic Chukkas feature an Atlas Tred outsole, plus nickel eyelets for durability throughout the chilly winter. While you might be better off wearing the Huckberry Duck Boots in an extreme blizzard, the Red Wing Heritage Classic Chukkas are as good as it gets the rest of the time. The plain toe chukka construction and briar oil slick leather are two touches that stand out subtly and stylishly, making them an easy bet to wear with everything from expertly faded denim and a grey crewneck sweater to your favorite henley and a tough waxed trucker jacket.
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Of course, the Red Wing Heritage Classic Chukkas can also be dressed up ever so slightly — try them with the Billy Reid Bond Peacoat, plus a classic Oxford shirt and slim tan chinos, for Sunday brunch or even a day at the office. Yes, Red Wing Heritage boots can work at the office — it’s possible, folks. Good luck out there, and let me know on Twitter if these boots work out for you.

SHOP: The Red Wing Heritage Classic Chukkas via Bespoke Post 

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See Now, Buy Now: The Red Wing Heritage Classic Moc Boots Are the Perfect Winter Boots to Buy Now

Red Wing Heritage

Rugged boots that’ll last all winter.

On the hunt for the perfect winter boots? Yes, that’s right — we said “perfect.”‘ Perfection is a very high bar to clear, admittedly, and yet there are certain brands, like Red Wing Heritage, that continue to strive toward that aim by sticking to what they know best. Now, we previously talked about the Red Wing Heritage Classic Moc Toe Boots as seen at the top of the page (in this post), but we’re back again to dive deeper today — they’re just that good. That’s surely lofty praise, but a classic brand like Red Wing Heritage can back it up — and it’s all the better that the Red Wing Heritage Classic Moc Toe Boots are but the latest release from the lauded company to land on your wish list of men’s style essentials. That’s what your humble author thinks, at least. Why’s that now?

SHOP: The Red Wing Heritage Classic Moc Toe Boots
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Well, my friends … the Classic Moc Toe Boots from Red Wing fit right in with the brand’s lineup of stellar boots … yet they stand out quitely in their own, very pleasing way. Much like the equally rugged and winter-ready Red Wing Heritage Rover Boots, the Classic Moc Toe Boots are made to lace up and get to work, starting with the Traction Tred wedge outsole for durability and grip on icy winter surfaces. The use of Goodyear welt construction also adds another dimension of toughness — yes indeed, these could be the  perfect winter boots.

And lest you expect anything but the best from Red Wing Heritage, these rugged moc toe boots are made with … yes, you guessed it — the brand’s iconic full-grain, oil-tanned leather, fashioned here into an incredible pair of everyday boots that you should wear as much as you can. What are my recommended pairings for the excellent Red Wing Heritage Classic Moc Toe Boots? That’s pretty easy, I think. Start with expertly faded slim blue denim, add a classic henley and throw on a rugged shawl cardigan.

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Or wear these boots with classic everyday chinos, a timeless chambray shirt and of course, an heirloom-quality peacoat. The details and construction are simply applause-worthy, meaning you should wear them all that much more. Heck, you can even try the Red Wing Heritage Classic Moc Toe Boots with a tailored charcoal flannel suit and a chambray dress shirt. Yes, yes you can — no doubt about.

Thanks for reading! Are these stylish leather boots making their way onto your feet this season?

SHOP: The Red Wing Heritage Classic Moc Toe Boots


Style Pick of the Week: Red Wing Heritage Rover Boots

Timeless, durable leather boots that pass every test you could throw at ’em. Image courtesy of Red Wing Heritage.

Let’s keep it simple to start today’s Style Pick of the Week off the right way, folks: For fall, you need nothing less than the Red Wing Heritage Rover Boots on your feet. After all, if you’re going to snap up a pair of stylish leather boots just in time for the season, you might as well make ’em the best of the best.  And if you read the blog at all, you’re aware that we’re all about quality, timeless materials and a distinct sense of versatility & toughness — all of which Red Wing Heritage stands by. And the Rover Boots in particular sit right in the crosshairs of what you should be looking for this fall — boots that simply won’t quit, the kind that’ll pair with your favorite dark denim and a flannel shirt or a thermal henley for weekend (and weekday) adventures aplenty. They’ll work with more outdoors-minded pieces like tough chore pants and a rugged flannel-lined trucker jacket, too. What separates the Red Wing Heritage Rover Boots from the rest of the pack?

SHOP: The Red Wing Heritage Rover Boots and Red Wing Basic Care Product Kit  

It’s simple: The same approach and attention to detail that makes any pair of boots from the brand tough to beat. The best boots for fall start with the best leather, and Red Wing sits at the top in that category — they make it look easy with full-grain, oil-tanned leather from their own Minnesota tannery. Goodyear welt construction, a process that allows the boots to be resoled after years of hard wear, also, sets the beautifully rugged Red Wing Heritage Rover Boots apart from the pack.

Red Wing Heritage

Another look at the workman-like profile of these tough leather boots.

The construction of these boots is notable for another reason — they’re, somewhat incredibly, water, stain and perspiration-resistant — yep, the Rover Boots are as tough and stylish as it gets. You’re also riding easy in terms of comfort: These durable boots are built from the ground up with a crepe rubber sole. So, you know they can stand up to most anything. Might I also suggest you snag a handy Red Wing product care kit to keep the Rover Boots looking fresh? That’ll do it. Heck, even the price is a selling point when it comes to the Red Wing Heritage Rover Boots — try finding a pair of boots like this for under $300 anywhere else. It’s tough to do, yes? I think you’ll agree with me when I say the Red Wing Heritage Rover Boots are all you need for fall, right down to the USA-made construction. Who else is ready to break out these handsome, rugged and stylish boots? I thought so. If you pick up these boots, keep me posted on Twitter. And thanks for reading!

SHOP: The Red Wing Heritage Rover Boots and Red Wing Basic Care Product Kit  

See Now, Buy Now: The Red Wing Iron Ranger Boots Are A Must-Have Classic for Fall

Red Wing Iron Ranger

An incredibly high-quality, long-lasting pair of stylish men’s boots from Red Wing Heritage.

Are there certain items, certain menswear essentials, that are truly timeless and averse to trends? In short: Yes. And my friends, the stunning Red Wing Iron Ranger Boots fall squarely in that camp — they’re absolutely one of the best pairs of men’s boots to buy now, and hopefully … for forever. That’s saying quite a lot, but there’s a reason they’re part of our ongoing See Now, Buy Now series: If I were, I’d buy the Red Wing Iron Ranger Boots right this instant. Durable leather boots like these are but one way to start getting ready for fall — so much of the fall season revolves around getting the details right in terms of fit, texture & rugged appeal, and the Red Wing Iron Ranger Boots have got all of that, and then some. They’re a timeless pair of boots for a reason: The silhouette is at once recognizable, functional and seriously stylish, and the specs on the Red Wing Iron Ranger Boots are investment-worthy. From the use of rugged Hawthorne Muleskinner leather — guaranteed to get better with age — to the Goodyear welt construction, these stylish leather boots have it all.

And the great thing about a durable, versatile pair of leather boots for fall, like the Red Wing Iron Ranger Boots? You can wear ’em with plenty of style essentials for the season. Take an indigo denim shirt and slim black denim, then add the Iron Ranger Boots, for instance — you’re ready for a night at your favorite brewpub or a rock show in equal measure. As far as other ensembles go, the Red Wing Iron Ranger Boots can pair up nicely with more rugged favorites, like a grey crewneck sweater, a thermal henley and tan chinos. See? Versatility at its finest. Heck, if you were feeling quite adventurous, I’d say you should trot out the Red Wing Iron Ranger Boots with a navy cotton blazer (like the Taylor Stitch Everyday Blazer) and a white Oxford if you work in a more casual office. Yessir — the Red Wing Iron Ranger Boots can do it all, nearly.

OK, let’s hear it — what are your thoughts on the Iron Ranger Boots? Are they on your fall style wish list?

Online Shopping Picks: The Best Men’s Chukka Boots for Fall

Editor’s note: For a full set of menswear shopping picks, click that link.

If you’ve followed along with The Style Guide since the very beginning (way back in 2013, folks), you might recall your author extolling the virtues of certain style essentials. Although there are basics like a classic blue Oxford and slim dark denim  for your top half, those essentials can be a bit more difficult to pin down in terms of footwear. Or are they? One of those key pieces is absolutely the chukka boot. Versatile, durable, wearable no matter the weather. That being said, there’s no better time to get your footwear wardrobe refreshed (or started, or added onto) than during the fall. It’s perhaps the best time of the year for menswear, what with layering and rugged textures galore — and even if you live in a temperate climate, maybe you’ve got a special place in your heart for today’s topic: The best men’s chukka boots for fall. The time just feels right to dive into a bevy of boots that can exude style both rugged and refined, dressy and casual. That’s darn near the definition of a style essential, and it’s as good of a place to start as any in today’s latest menswear shopping picks entry. Of course, there are all kinds of other boot styles out there for fall and winter (wingtip boots, anyone?), but rest assured we’ll get to those in good time. Want to see how to style chukka boots? Head to Instagram or search this site’s archives (or heck, head on over to Twitter, too).

#1. Thursday Boots Whiskey Scout Boot — $149

A rich pair of brown leather chukkas practically made for fall.

A rich pair of brown leather chukkas practically made for fall.

Having tried everything from the much-loved Roughout Captain Boot to the dependable Suede Scout Chukka, this #menswear writer can definitely vouch for the value inherent in Thursday Boots’ footwear assortment. Checking out the Brown Scout Chukka during a spring trip to Washington, D.C. sealed the deal for me as far as the brand’s chukkas go, and it’s very safe to assume that the rich Whiskey Scout Boot will perform much the same. The color is, quite simply, handsome and very wearable with everything from crisp olive chinos and a cream cable sweater to a worsted wool suit. For the price, that’s applause-worthy.

#2. JackThreads Mac Desert Chukka — $80

A new footwear introduction from a brand that can do just about everything.

A new footwear introduction from a brand that can do just about everything.

It might not surprise you to read that JackThreads made an Online Shopping Picks entry on this site. However, what might come as a shock is that the much-loved E-commerce retailer now has a line of footwear to back up the rest of its affordably priced, stylish menswear line.  Let’s start with the important stuff. First off, that combination of looks and price — can’t beat it. $80 for a chukka that bears the JackThreads name is A-plus, truly. The lower profile, Taupe colorway and crepe sole make them the ideal weekend chukka — pair them with a broken-in pair of blue denim and a crewneck sweater for a put-together casual look, or mash them up with slim wool trousers and a navy cardigan to head back to the office. Oh, and pick up a second pair while you’re at it — did we mention the excellent price?
Buck Mason - Timeless Design. Made in America.

#3. Johnston & Murphy Copeland Chukka — $155

Equal parts casual and sharp.

Equal parts casual and sharp.

If the Thursday Boots chukka seen at the top of the page is a dressy chukka boot, and the JackThreads chukka boot seen here above is a casual chukka boot, the Johnston & Murphy Copeland Chukka is something of a hybrid. Featuring  a deep red-brown oiled nubuck that should break in beautifully, the contrast stitching and crepe sole give it a casual feel. But make no mistake, this is a still a dependable leather chukka boot you should pair up with navy suit trousers and a grey cardigan, or a broken-in pocket tee and dark denim for weekend errands.
Buck Mason - Timeless Design. Made in America.

#4. SWIMS Barry Chukka in Taupe/Biscuit — $230

Casual, reliable and waterproof, all at the same time.

Casual, reliable and waterproof, all at the same time.

Chukka boots that offer a little bit of everything are nice to have on-hand — especially if your fall adventures take you everywhere from a football game to park hikes to pumpkin patches (yes, we’re going there already). In particular, these SWIMS chukka boots are fully waterproof, and combine the styling potential of a casual crepe sole with the functionality needed for tricky fall weather. The silhouette feels more like a sneaker than a classic chukka boot, and that’s not a bad thing — this pair would work especially well with burgundy corduroys and a long-sleeve merino tee for aforementioned weekend adventures.

Related: The Best Suede Chukka Boots to Buy Right Now

#5. Red Wing Heritage Weekender Chukka — $230

A unique chukka boot that works for both spring and summer style scenarios.

A unique chukka boot that works for both spring and summer style scenarios.

If you perused the pages of this site back in July, you’re familiar with the Red Wing Heritage Weekender Chukka. It’s a lighter-weight chukka boot that works equally well in the spring and summer as it does during the fall and winter — that makes it worth the price alone. It’s a new addition to the Red Wing Heritage line that plays off the brand’s rugged heritage while offering up a bit more flexibility and comfort than a thick-soled pair of winter boots. We’ll get to that point in the season eventually, but for now, know that you just might have a chukka boot fit for adventures seven days a week — and then some. They’re the ideal complement to classic navy chinos, and they’ll put in plenty of hours beneath trusty dark denim and a slim fall flannel shirt.

Did the above list of the best men’s chukka boots get you thinking  a bit? A trusty pair of chukka boots can seriously become a multi-day workhorse in your footwear arsenal, easily wearable with business-casual or weekend-casual outfits. Embracing the changing seasons can be a whole lot easier if you have the right gear to wear, too. That certainly starts with a rugged, dependable pair of chukka boots – after all, there really aren’t too many fall-centric outfits that don’t start with a great pair of boots (or maybe that’s just your author’s opinion). And with such great variety on the market — from a fresh style done by a heritage brand to an entirely new E-commerce offering from JackThreads — there are plenty of picks worth exploring. Want to share your own? Leave a note in the Comments section below!

Until our next menswear shopping picks post — coming next week — stay tuned for the Friday Read, and stay stylish.