The Sunday Sale: Save 30 Percent On Some of the Best Hiking Boots for Men at Huckberry

When the going gets tough, when the streets seem too slick or the road seems too steep, that’s where your menswear essentials really need to go to work. Of course, if you read the blog, you know this all too well, and that process often starts from the ground up with a pair of the best men’s boots. Or rather, with a pair of the best hiking boots for men, at least in the case of today’s post.

Astorflex Rockflex Hiking Boots.

And the casually rugged, highly functional pair in question clocks in from a brand you know and love: Huckberry. Oh, and a retailer you know and love: The family-owned, crafted-in-Italy makers behind Astorflex, who already happen to make some of your favorite chukka boots.

It might seem tricky for a brand largely known for a more casual crepe rubber sole chukka boot to craft a stylish pair of men’s hiking boots, but rest assured that Huckberry knows what it’s doing. Suffice to say, the Astorflex Rockflex Hiking Boots can definitely be trusted.

And here’s the even better part: Since it is in fact the Sunday Sale here on the blog, your new favorite pair of hiking boots are now 30 percent off.

That drops them below $230, which is a downright steal for rugged hiking boots built on a commando rubber sole, which are then fully lined in leather and finished with antique eyelets. Those are specs that can stand up to much more expensive pairs of hiking boots on the market, so in the spirit of getting out there and getting after it this winter, shop now and save big before winter rolls into town by scoring a pair of the Astorflex Rockflex Hiking Boots.

Style Pick of the Week: Red Wing Heritage Classic Chelsea Boots – The Only Boot You’ll Need This Winter

I’d wager that if you’ve been reading this blog frequently and searching for the best menswear essentials and the best men’s boots, then you don’t need me to tell you twice: The right pair of boots can make all the difference as you deal with winter weather and harsh conditions. If you’ve learned that truth the hard way and could use an upgrade in your boot rotation though, you’ve come to the right place.

Red Wing Heritage Classic Chelsea Boots.

And the brand here to assist in that upgrade is a certified American classic — and one of my favorite boot brands, aside from that. We’re talking today about Red Wing Heritage, a company renowned the world over for its long-lasting, tough-as-nails boots — a company that can be found, of course, within the digital menswear mecca that is Huckberry.

That’s where we’ll start our journey into the world of Red Wing as we consider the Red Wing Heritage Classic Chelsea Boots.

The Red Wing Heritage brand name nearly speaks for itself, with roots making boots for linemen and outdoorsmen in Minnesota and then, across the globe. They still follow many of those same processes today to craft some of the best American-made boots on the market.

Best Red Wing Heritage boots for men.

That’s a true rarity when you consider that even many of the best boot brands for men are using production methods in countries like Mexico (high-quality methods, at that, but nonetheless!). The Red Wing Heritage Classic Chelsea Boots follow closely along those same lines: Remarkable production methods, expert quality and excellent longevity.

Specifically, the Red Wing Heritage Classic Chelsea Boots are made with a recraftable Goodyear welt design that means the boots can be resoled, and the outsole itself is the brand’s TractionTred design.

That design should provide excellent traction on slick city streets this winter, while rich oil-tanned full-grain leather — the same kind Red Wing has been using for decades — only elevates these boots even further. The Red Wing Heritage Classic Chelsea Boots are the perfect hybrid between rugged work boots and slightly more dressy Chelsea boots.

Best Red Wing Heritage boots for men.

These would pair best with your favorite pair of dark blue jeans, a classic henley and one of the best waxed trucker jackets, but the Red Wing Heritage Classic Chelsea Boots could also be styled up with tobacco-colored chinos, an Oxford shirt and one of the best shawl cardigans.

Dress ’em up slightly, dress ’em down for days in the yard or keep ’em classic to head out for a casual evening — the Red Wing Heritage Classic Chelsea Boots deserve to be worn as often as possible this season, whenever you might need them.

The Thursday Buy: Amberjack Just Introduced Its First Lace-Up Boot, And You’ll Want a Pair ASAP

Best new lace-up boots for men.

If you keep a close eye on the pages of this blog, you’ll know that I’m all about finding brands and products you love, and then consistently going back to those same brands and products on the daily. It just makes perfect sense, right?

Satchel and Page

Consistency is key, finding items you can wear as often as possible is essential, and it’s an even bigger deal when a brand you love — perhaps, say, a brand that makes some of the best men’s dress shoes — steps up and expands into a new style while staying true to its roots.

That’s certainly what we’re seeing today on the blog from Amberjack, the Brooklyn-based upstart known for making some of the best lace-up dress shoes and the best loafers. I’m a fan of both styles in terms of comfort and quality right out of the box, but the NYC-based shoemaker just upped the ante even further.

You see, Amberjack just debuted the Amberjack Boot, a new boot addition alongside its wildly successful Amberjack Chelsea Boots (which are some of my personal favorite Chelsea boots). All the while, they’ve done it as they’ve introduced the brand to a new, tech-forward way to look at leather shoes (at least, that seems to be the case from my perspective).

Best leather lace-up boots for men.

If you’ve been fortunate enough to try Amberjack (the brand’s dress shoes sell for a highly accessible $195), you’ll know that quality, comfort and innovative technology rise to the forefront. While old-school boots — many of which I love! — are rugged, built with thick, sturdy soles and tough leather, the Amberjack Boot has more DNA in common with modern sneaker-boots, as does the rest of its lineup.

Amberjack boots review.

That doesn’t mean they sacrifice style in the slightest, but technical prowess is precisely what separates the Amberjack Boot from other pairs of the best men’s boots. The Amberjack Boots feature the brand’s signature dual-function athletic outsole for some true spring in your step, and the heat-activated insole molds to your foot over time and feels supremely comfortable right out of the box.

Like Amberjack dress shoes, the Amberjack Boots are the kind of pair you can slide into and wear properly right away, no break-in time required. They feature captoe detailing for extra reinforcement and a stylish touch, and full-grain leather throughout the upper should both age nicely and last quite a while with the Amberjack Shoe Care Kit, too.

Best men's leather boots for winter.

It’s as if the brand has thought of everything when it comes to the Amberjack Boots, right? And with their relatively streamlined yet versatile toe shape, these boots should more than pass muster alongside a range of style staples, be it your favorite cordury pants or dark blue jeans and a classic henley.

Plus, like the full range of Amberjack dress shoes, you can find some of the best men’s boots in the company’s rich Chestnut leather, plus two dark shades of black and a subtly textured Copper nubuck leather option. Hopefully, this is enough to convince you to take the plunge and secure a pair of the Amberjack Boots — and at the more-than-agreeable price of $205, it sounds like they’re a downright steal and a fine addition to any footwear rotation.

See Now, Buy Now: The Red Wing Heritage Classic Moc Toe Boots Are a Certified Fall Classic

Red Wing Heritage moc toe boots review.

When the going gets tough, the tough lace up a pair of the best boots for men from Huckberry. Or at least, that’s what I say. And the tough (and stylish, like yourself!) more specifically lace up a pair of impossibly rugged Red Wing Heritage men’s boots. Let’s go beyond that, though.

The legendary Minnesota brand has been making some of the finest boots on the market, right here in the States, for decades, with an emphasis on rich leather, the finest materials and the best construction around. Of course, if you read the blog, you already know that, but a reminder is always savvy, no?

That makes the Red Wing Heritage 6-Inch Moc Toe Boots a certified classic in every regard (as the headline notes), complete with sturdy contrast moc toe stitching, a handsome, rich Alpine Portage leather build, and the durability to stand up to just about anything this season. This pair of the best boots for men nearly speak for themselves, which is why I’m wrapping up this post in due time right about… now. Lace ’em up and get out there this season, folks.

Style Pick of the Week: Billy Reid Indianola Chukka – A New Classic Pair of Fall Boots

Best fall chukka boots for men.

I’d guess that, if you read the blog on the regular, your wardrobe has more than a few of the best men’s style essentials, particularly on the footwear front when it comes to, say, the best chukka boots for men. But what about when things get shaken up a bit and your favorite menswear designer re-enters the men’s footwear space in a big way, just in time for fall?

That’s what Alabama-based Billy Reid is doing with the reintroduction of Billy Reid footwear, which should provide plenty more competition for your rotation of the best men’s boots. Let’s take a closer look, shall we?

Best leather moto boots for men.

Now, I already wrote about new boots from Billy Reid yesterday on the blog, but let’s talk about a highly versatile pair in particular. After all, the collection includes just two new pairs for now: First up, we’ve got the Billy Reid Paglia Moto Boots, made in Italy from overdyed pebbled leather with a slight edge to it.

Those boots are sleek and dressy yet road-ready, but we’re here today to talk about the Billy Reid Indianola Chukka Boots. They’ve certainly got the pedigree you’d expect from a designer known for making one of the best pea coats and the best dress shirts on the market,

The Billy Reid Indianola Chukka Boots are very nearly what you’d precisely expect from a designer with a commitment to timeless style and craftsmanship. Light brown kudu leather gives these a bit of texture right out of the box, but these stylish men’s chukka boots will develop their own distinctive patina over time.

Best men's chukka boots.

Comfort flex soles provide ease of movement out of the box — these shouldn’t feel overly stiff or uncomfortable. The famed menswear brand has even burnished the toe cap for a bit of a rugged-meets refined feel when it comes to the Billy Reid Indianola Chukka Boots.

Satchel and Page

The profile on these should prove streamlined enough to dress up with the best corduroy pants or your favorite pair of chinos, yet classic brown leather chukka boots also wear very well with timeless dark blue denim.

Keep in mind that although the Billy Reid Indianola Chukka Boots are an investment (they’ll set you back $448), you’re getting a truly classic pair of men’s boots that can be dressed up or down, a pair that’s made in Italy from the finest materials on the market. It sounds to me like your new favorite pair of chukka boots could be just a few clicks away.

The Friday Read: New Men’s Footwear from Billy Reid & Classic Fall Whiskey from Castle and Key

Billy Reid men's footwear.

My friends, here we are on the brink of what promises to be another most excellent fall weekend — it might be a blustery and rainy one in New York City yet again, but I’m equipped with the proper fall style essentials for the task at hand, including my trusty Shinola leather watch (and many more).

Best chukka boots for men.

With today’s post (or yesterday’s post on the best shirt jacket for men), hopefully, you feel the same way. On that note, let’s talk some of the best fall boots — and from an unlikely source, at least until recently: Billy Reid. You see, the famed Alabama-based menswear designer, one of my favorite brands and menswear companies, period, hadn’t made footwear in recent years — that all changes now though, with two classic styles that should cover plenty of style scenarios.

Billy Reid footwear now includes both a sleek pair of leather moto boots and a stylish pair of chukka boots, and you can certainly look for much more on two of the best pairs of shoes for men this weekend on the blog (hint, hint). I don’t know about you, but it’s an exciting prospect that one of the best menswear designers in the country is now making some of the best men’s boots — it’s almost worthy of a toast, don’t you think?

And a toast or two was once again the focus of my week, as I trekked to the lovely, rolling hills of Kentucky and Bourbon Country itself. The mission? Visit the historic Castle & Key Distillery outside Lexington as part of my spirits and freelance writing pursuits, a trip that included a tour of its famed grounds and plenty of sipping on Castle & Key Restoration Rye.

Speaking of rye whiskey, you should also check out my latest Maxim.com feature on an excellent new rye whiskey from the spirits innovators at BHAKTA. But in the meantime, back to Castle & Key.

We also visited charming Lexington restaurants like Eppings on Eastside, and spent a very memorable day sipping bourbon and watching horse racing at the iconic Keeneland race track. Consider this just a taste of what’s to come regarding this heralded, fast-growing spirits company.

It was once again another reminder that I’m so fortunate to do what I do, be it covering menswear on this very blog or trekking around the country visiting the best distilleries and menswear factories in the business.

For now, I’m going to put some Billy Reid men’s boots on my wish list, and later, I’ll be enjoying some Castle & Key bourbon on a crisp fall night. I hope you consider doing the same! Cheers, and thank you for reading!

The Tuesday Steal: Get Up to 65 Percent off the Best Men’s Boots for Fall At FRYE

Best men's boots for early fall.

A crisp, bright fall day dawns, you reach for your new favorite trucker jacket and a classic pair of blue jeans, and then you realize: Your boot rotation could use a bit of an upgrade. Or rather, your selection of the best men’s boots could stand to deliver some nice bang for your buck, to go along with style points and seasonal, rugged appeal.

Allow Northeast bootmakers FRYE to sort out the last part of that equation in fine form — all the while allowing you to save a buck or two in the process. Famed Massachusetts-based FRYE, makers of some of the best men’s chukka boots (and leather sneakers, and rugged lace-up boots, and much more!) have a knack for blending heritage quality and rich leather with long-lasting dependability.

When you shop FRYE, you’re getting a pair of boots that are on-trend, made to last and always tasteful. And they’ve doubled down on that aim at the best time possible: The FRYE End of Season Sale is giving you the chance to score a new pair of boots for as much as 65 percent off.

Yessir, you read that correctly: Use the code LASTCALL to get an extra 20 percent off men’s sale boots, for a grand total of up to 65 percent off your new favorite boots. Let’s take a closer look at the stellar, stylish men’s boots you should have on your radar today, shall we?

Best Chelsea boots for men.

You’ll find a nice array of classic-yet-modern styles within the FRYE End of Season Sale, but in my experience, it’s wise to opt for a versatile pair you can dress up or dress down, especially when you’re dropping close to $300 full price at FRYE. And which pair of stylish men’s boots checks the right boxes today at the FRYE End of Season Sale?

That’d be the FRYE Tyler Chelsea Boots, which are crisp enough to dress up with slim chinos or corduroy trousers, and casually cool enough to wear with your favorite pair of blue jeans and the aforementioned essential waxed trucker jacket for fall.

Plenty of FRYE hallmarks are on display with these Chelsea boots, from the soft leather upper to the supple leather-lined footbed and a rubber-injected outsole forepart, geared to provide comfort and rebound. In my experience, that design detail makes these FRYE men’s boots comfortable out of the box, while the leather is smooth and soft, rather than overly stiff.

FRYE Chelsea boots review.

Helpfully, the FRYE Tyler Chelsea Boots are also available in a pleasing array of leather colors, including a burnished Khaki (on sale for $207.98 now via the FRYE End of Season Sale) and various shades of broken-in black, brown and tan.

Part tailored jacket, part sweater, all versatility.

Could they be your new go-to fall boots? Between the clean silhouette, the reliable 6-inch shaft height and grippy outsole, and the rich leather, I’d say you’re way ahead of the game as you plan out your next fall #OOTD.

The Thursday Buy: The HELM Boots Hynes Boots Are a Must-Buy Pair of Fall Boots

Best leather chukka boots for men.

Every guy needs a reminder every so often — a reminder about tried-and-true seasonal style essentials, like the best boots for men. Of course, we’ve been diving plenty into the season’s most necessary, stylish footwear these past few weeks, but if you ask me, a guy can never have too many rugged leather boots close at hand. And that’s what’s so great about the HELM Boots Hynes Boots.

In my experience, these boots check all the right boxes in terms of form and function, boasting richly crafted, supple leather and a comfortable ride underfoot. The list only grows from there, so let’s count the ways, shall we?

We previously talked about the lace-up, captoe HELM Boots Lou Teak Boots, which offer rugged appeal in spades, but the more streamlined HELM Boots Hynes Boots are a dressier and more streamlined touch.

HELM Boots for men review.

The HELM Boots Hynes Boots use the brand’s softest-ever leather (Neymar, for those keeping score at home) while also rounding things out with a padded collar for comfort. They’re also fully lined in leather for a soft and supple feel out of the box, and the eyelets even forgo hardware to keep the look clean and sleek.

The same holds true for the profile, which you could easily style with your favorite blue jeans as readily as the HELM Boots Hynes Boots can be worn with some of the best corduroy pants on the market. And at $250, these sleek-yet-rugged leather chukka boots for men are an exceptional value, especially considering the fact that they can be resoled over time.

In the case of (potentially) your new favorite leather chukka boots, it turns out that a reminder is a great thing to receive, right? Yessir. Happy fall, and happy shopping over at HELM Boots, folks.

See Now, Buy Now: The Taylor Stitch x Danner Ridge Boots are the Coolest New Fall Boots to Buy Now

There are surely more than a few style situations on the horizon for you this fall (and myself!) that are going to require you to lace up a pair of the most rugged boots for men. It could be something as light-spirited as a brisk morning tailgate, something in-between like a coffee shop visit and brewery beers, or something more hard-wearing, like a day hike or a upstate getaway.

For those situations and more, meet your new favorite pair of boots, courtesy of Taylor Stitch and Danner.

The two standout West Coast brands — Danner with decades of Pacific Northwest bootmaking excellence, Taylor Stitch with nearly 15 years of crafting the best modern menswear — teamed up on the new Taylor Stitch x Danner Ridge Boots.

The resulting pair is an ode to Danner’s lightweight Ridge Hiker, with customary Danner performance details (the brand makes some of my favorite pairs of men’s boots), not to mention Taylor Stitch’s uniquely stylish point of view. And the Taylor Stitch x Danner Ridge Boots fit nicely in both worlds, with the proper style details and performance specs to match.

Taylor Stitch x Danner Ridge Boots 2023.

The Taylor Stitch x Danner Ridge Boots start from the ground up, literally, with a sturdy yet comfortable Vibram® Kletterlift Thin outsole, the kind that can grip slippery terrain with ease. For even more comfort, they’re amped up with a removable Ortholite footbed, while a GORE-TEX waterproof liner keeps your feet dry. The rich dark brown pebbled leather is distinctive and will develop a handsome patina with age, but it’s the dry-waxed camo side inserts that give these boots an extra dash of style.

Part tailored jacket, part sweater, all versatility.

The Taylor Stitch x Danner Ridge Boots are resoleable, which is great news — you’ll have these USA-made men’s boots for years to come. Speed hooks deliver a secure fit and a classic hiking boot touch, which is ideal for even more stability on uneven terrain.

Of course, you can rock the Taylor Stitch x Danner Ridge Boots more simply, say with a pair of Taylor Stitch indigo denim and a Taylor Stitch workshirt, for easygoing fall pursuits aplenty. Get ahead of the curve and invest in the best for early fall with the latest and greatest from Danner and Taylor Stitch.

The Sunday Sale: Get 20 Percent off Best-Selling Men’s Boots at Wolverine

What’s a guy to do to get ready for fall in style? Well, in my opinion, it’s all about finding brands you can trust, using a little know-how and evaluating your wardrobe’s needs right this second. It might seem tricky to do as we move into fall — it’s easy to feel a step behind if you haven’t quite yet secured that pair of the best fall boots to really lace ’em up in rugged fashion, for instance.

Best Wolverine boots for men to shop now.

And yet to those concerns, I say fear not, because it’s certainly still possible to shop a pair of in-season, of-the-moment rugged boots for men with plenty of functionality and even style in spades. That’s where Wolverine comes in.

The Michigan brand has been a favorite of mine for over a decade, yet it can be tough to score savings on this famed foot brand. Until today, that is: You can use the code 20BESTSELLERS to get, well, 20 percent off some of the best boots for men, just in time for the season ahead.

This encompasses plenty of the trusty boot brand’s top workwear styles, yet there are options that merge both utility and rugged fashion, like the Wolverine Loader Wedge Boots.

Best rugged moc toe boots for men.

Made from premium leather atop a Goodyear welted sole for durability, that same outsole is slip-resistant for inclement weather. A padded collar offers a comfortable, secure fit, while contrast moc-toe stitching (double and triple-stitched in key areas for toughness) provides both visual appeal and style.

These are some of the best men’s boots to wear with jeans and your favorite henley or flannel shirt (or both). The Wolverine Loader Wedge Boots are but one pair up for grabs at 20 percent off with the code 20BESTSELLERS, so act swiftly to secure your new favorite pair of fall boots today, my friends.