The Thursday Buy: These Sperry x Huckberry Chukka Boots are A Rugged Update to a Classic

Huckberry x Sperry chukka boots.

If you thought it was nearly impossible to improve upon the best men’s style classics, think again. The humble chukka boot has a storied heritage all its own, as does American footwear maker Sperry, innovators of styles like the boat shoe and of course, the Sperry AO Chukka. So, what does one get Huckberry and Sperry team up on a refresh to an iconic fan favorite?

Well, the answer is pretty clear right up front with the new Sperry x Huckberry AO Chukka Boots, a meeting of the minds that blends history, rugged appeal and a few fresh, revamped touches in one stylish pair of men’s boots.

Huckberry, everyone’s favorite adventure-and-Americana retailer, with a healthy respect for timeless styles (like Sperry boat shoes), says that the AO Chukka goes one step further in terms of style, sensibility and even performance.

Sperry x Huckberry boat shoes.

In fact, one of the best online retailers for men says that the Sperry x Huckberry AO Chukka Boots take “everything you know and love about a boat shoe—like the hardwearing, water-resistant leather uppers and ultimate-gripping outsoles—and combines it with the easy styling of a chukka.”

Sperry chukka boots for men.

That’s not a bad look for your footwear rotation this season and well beyond, right? No doubt about it. The handsome Sperry x Huckberry AO Chukka Boots get plenty of things right when it comes to the details and their design, including collaborative detailing inside the heel and on the tongue.

There’s a laundry list of features to love, including rich full-grain leather throughout — the kind that’ll develop a handsome patina over time — as well as the use of traction-friendly Razor-Cut Wave-Siping technology for grip on slick streets in winter, spring and, well, just about any season. Of course, rawhide laces and contrast stitching throughout, just like you’d find on classic moccasins, drive home the craftsmanship and timeless appeal of the new Sperry x Huckberry AO Chukka Boots.

What’s even better still is the fact that they’re up for grabs for under $200, and there are plenty of sizes to be had when it comes to your new favorite chukka boots. A meeting of the minds that bridges the gap between the old and the new, done by one of your favorite retailers? Sounds like your next footwear purchase has arrived, my friends.

The Sunday Sale: These Durable, On-Sale Forsake Boots from Bespoke Post Are Perfect for Winter Adventures

Best outdoor boots for men.

Especially in these brisk winter months, the focus is almost always on building an outfit from the ground up, or at least, an outfit to take on the elements. Blustery snow drifts, slick city streets and frigid mornings on upstate getaways call for one thing, and one thing only — a pair of the best winter boots, like the kind my friends at Bespoke Post sell.

Or at the very least, you should certainly have your heart set on boots with enough traction and performance to get you from point A to point B when the situation calls for it, and that’s where we step off the trail and into today’s post in earnest.

And when you really get down to it, those boots had better be waterproof, traction-ready and tough as heck — the good news is, the Forsake Cascade Peak Mid Boots are all of that and then some. Oh, and since this is a Sunday at The Style Guide, they also happen to be on sale — just in the nick of time, right?

While the performance-focused Forsake Cascade Peak Mid Boots aren’t as insulated as a pair of shearling boots or even some faux-fur or shearling L.L. Bean Boots, they’re a worthy option if there’s not a foot of snow on the ground, especially if your winter pursuits call for sporting adventures and casually rugged style.

They boast the modern appeal of sneakers and the functionality of hiking boots, and it doesn’t hurt that the Forsake Cascade Peak Mid Boots are 40 percent off right now at Bespoke Post — good news indeed for your wallet after the holiday rush, right?

They’re also as functionally minded as it gets, from the taped seams on the leather and heathered textile upper to the durable MultiGrip rubber outsole and compression EVA midsole — talk about comfort and traction to the max, my friends.

For good measure, recycled PET laces and linings add a sustainable touch, and it doesn’t hurt that these boots still boast a rather streamlined profile compared to other hiking boots on the market. Plus, come springtime, the Forsake Cascade Peak Mid Boots will be more than ready to take on that first lovely trail hike when the snow melts — at 40 percent off right now, that doesn’t sound like a bad way to plan for the present or the future, right?

See Now, Buy Now: These Frye Tyler Chelsea Boots are the Refined Option to Add to Your Wardrobe Now

Best Chelsea boots for men.

As we move slowly but surely into a new year, I find that sometimes, menswear reminders are helpful — the chance to get back to basics, the chance to rediscover old favorites and yes, the chance to finally pull the trigger on a style you’ve been coveting.

Perhaps that includes a style like a pair of the best Chelsea boots for men, with loads of versatility, an edgy appeal and the chops to be dressed up or dressed down. It might seem a high bar to clear, but this pair from the Northeast’s own Frye checks off all the proper boxes, and then some.

It’s not the first time we’ve talked about Frye Chelsea boots here on the blog, and it surely won’t be the last, because the Chelsea boot is an all-time great style with longevity and looks. In the case of the Frye Tyler Flex Chelsea Boots, you’re getting heritage quality, superior craftsmanship and an iconic silhouette — not a bad way to start the year off on the right foot, is it?

The key with these Chelsea boots in terms of comfort and wearability lies in the new, flexible rubber outsole, which moves with you and provides standout traction on slick city streets. Combined with a variety of leather options — from a textured dark brown to a slick and shiny shade of brown with a dressy hue to it — and you’ve got options when it comes to selecting your preferred pair of these Frye Chelsea boots.

The 1-inch heel is nicely sized, not too tall nor too short — the durability of a sturdy pair of boots is crucial on slippery city streets, this winter, is it not? Complete with a leather lining, this set of Frye Chelsea boots should prove stylish, sharp, reliable and well-made — season after season, starting right now. Find your new favorite pair of dressy winter boots ASAP, my friends.

The Sunday Sale: You Can Only Get these Blundstone Boots at Huckberry, and they’re On Sale Right Now

In my experience, it’s often nice to know you can turn to a go-to, essential pair of boots time and again without missing a beat –not unlike my trusty Blundstone boots, which I wear about as often as possible (and which you can conveniently find online with just a few clicks via famed retailer Huckberry).

You see, when bad weather strikes, when all-day comfort is key and when casually rugged style is of the essence — which it often is here on this Brooklyn style blog — then a pair of Blundstone Chelsea boots just plain old work, at least in my experience.

Best Blundstone boots for men.

And if you haven’t dipped your toes, literally, into an on-trend yet classic pair of Blundstone boots, my friends at Huckberry have precisely what you need: That is to say, they’re now selling the Huckberry-exclusive Blundstone 2406 Suede Chelsea Boots, and it’s your lucky day.

How so, Well, those rugged Chelsea work boots are on sale, and at more than 30 percent off, they’re a downright steal (an understatement, of course).

The Blundstone 2406 Suede Chelsea Boots rethink what you thought you knew about the style — first off, they’re built with water-resistant suede, rather than a suede leather that’s difficult to care for when inclement weather rolls around.

Blundstone 2406 Suede Chelsea Boots review.

They also boast a shock-absorbent, extremely cushioned outsole, the kind that I love for its rebound, support and grip. The Blundstone 2406 Suede Chelsea Boots come in a wear-with-practically-anything shade of dark tan Sepia, while front and back pull tabs make for an easy-on, easy-off wearing experience.

They’re sturdy enough for work, stylish enough for a night strolling cobblestone streets in search of an Old Fashioned, and certainly worthy of your hard-earned cash given the fact that the Blundstone 2406 Suede Chelsea Boots are on sale right now at Huckberry, just in time for winter, the holidays and well beyond.

The Sunday Sale: These Stylish Sanders Boots are Up for Grabs at a Steal from Huckberry

I often turn to reliable classics in my style wardrobe as the temperature plummets, and that’s perhaps on display more than ever as I consider a selection of the best men’s boots for rugged refinement, versatility, comfort and a bit of work (and yes, play as well).

I’ve often found that the good folks at Huckberry have a knack for stocking and selling some of the best boots for men, including the Sanders Wilson Apron Derby Boots as seen above. These apron derby boots, so name for their open lacing system and moc toe construction, hit the right notes between rugged and refined in pleasing fashion, with a profile that can be dressed up or dressed down with ease.

Sanders men's boots review.

Better still when it comes to the easily wearable Sanders Wilson Apron Derby Boots is their durability — an unlined leather upper should break in wonderfully as the insole molds to your foot over time, with a design that’s neither too streamlined nor too rugged.

Note the studded rubber outsole for added traction, plus other carefully handcrafted touches that could only come from a family-owned British shoemaker with generations of experience in the category.

That means that, at least in my experience, you can style the Sanders Wilson Apron Derby Boots with everything from wool trousers and a herringbone blazer to cuffed selvedge jeans, a thermal henley and the famed Flint and Tinder Trucker Jacket for expert seasonal style.

We haven’t even covered off on the best part — the Sanders Wilson Apron Derby Boots are on sale right now via Huckberry in a rich shade of brown leather for the ultimate in seasonal style, particularly as you look for tips on how to dress for Thanksgiving (for instance).

The Sanders Wilson Apron Derby Boots happen to be about 25 percent off as we speak, so it’s no wonder they’re selling quickly at the moment to guys who want versatility and dependability in boots, in spades. Lace ’em up and see what wonders they can work in your winter wardrobe.

The Tuesday Steal: These Rugged Taylor Stitch Ranch Boots are 40 Percent Off Right Now

Taylor Stitch men's boots review.

There’s perhaps never been a better time than right now to get a deal on some of the best boots for men — or the best on-sale menswear, period — from one of your favorite retailers. That retailer in question? It’s Taylor Stitch, of course, purveyors of some of the most rugged fisherman sweaters, tough waxed jackets, sturdy shirting and now, some of the best boots to buy on sale.

You’ve very likely shopped plenty of Taylor Stitch menswear over the years, what with the brand’s focus on expertly cut shirting and outerwear in helpful chest sizing, but what about the fast-selling array of Taylor Stitch boots?

I’ve had the chance to try Taylor Stitch over the years when it comes to my own footwear rotation, and believe me when I say that you should take any chance possible to score savings on the San Francisco company’s rugged men’s boots.

Some of these styles can be found right now at a discount in the Taylor Stitch Last Call section, which is worthy of your time if you want savings on a stylish plaid buttondown, on cozy lounge pants or even on some cabin-worthy knitwear. But back to your footwear rotation — durability, toughness and style go hand in hand with Taylor Stitch men’s boots, and that certainly holds true with the Taylor Stitch Ranch Boots.

In my experience, the Taylor Stitch Ranch Boots boast expert construction — not unlike the brand’s shirting and outerwear, and that goes for the soft leather lining as much as the durable waxed suede exterior. The Taylor Stitch Ranch Boots are weather-ready and built to last, with a sturdy Vibram lug outsole and Goodyear-welted construction — the kind that’s fit for years of wear.

The profile is reminiscent of a work boot, but the overall style can be dressed down with jeans or dressed up with your favorite chinos — that’s about as versatile as it gets, and since they’re on sale right now for 40 percent off, that’s as striking a deal as you’re apt to find.

The Tuesday Steal: Save on these Dependable Blundstone Boots Right Now Through Todd Snyder

Blundstone men's boots review.

I don’t know about you, but I frequently find myself reaching for men’s style essentials I can count on in the clutch, the sort of pieces I can reliably wear over and over — especially in casually rugged situations, as with my Blundstone boots. The same can be said for American designer Todd Snyder’s collections, and the two come together nicely today on this fine Tuesday.

As wearable with dark blue or mid-wash blue jeans as they are with the right pair of canvas work pants or even stretch five-pocket pants, my Blundstone 558 Chelsea Boots might just be my go-to pair of footwear, the pair I wear more than any other.

If you feel the same way, and if your particular pair could use a refresh this fall, then you’re going to want to keep scrolling: The Blundstone 558 Chelsea Boots are now up for a rather rare discount via Todd Snyder. It makes perfect sense that the famed American designer would stock and sell the brand, since he tends to lean on classic, heritage-minded designs with pedigree of their own.

That holds true for his collaborations with Timex and P.F. Flyers over the years, as well as his penchant for selling brands he knows and loves — like Blundstone, of course.

Blundstone 558 Chelsea Boots review.

You need only dive into the selection of Todd Snyder shoes found online right now to see that it makes perfect sense for Snyder to stock and sell the Blundstone 558 Chelsea Boots in a rich black colorway. Made from water-resistant leather and featuring a tough, grippy TPU outsole, they’re ready to stand up to days in the yard tackling housework as easily as they can take you to a brewery or a rock concert.

I’ve also found that my Blundstone boots get better and more supple with age, and that’s quite the benefit when it comes to the best boots for men. If that sounds like utility your footwear rotation could use, then the Blundstone 558 Chelsea Boots are the pair for you — find ’em in select sizes on sale at Todd Snyder now.

See Now, Buy Now: The Allen Edmonds Higgins Mill Boots are a Timeless Fall Classic

When you come across a true men’s style classic, you tend to recognize it right away — and in the case of the best fall boots for men, those classics tend to hail from a heritage-minded company like Allen Edmonds. The Port Washington, Wisconsin company has been doing things the right way, the hard way since 1922, when Elbert W. Allen founded the Allen-Spiegal Shoe Company.

The rest isn’t merely history — there’s a sense of long-lasting style, quality and durability in every stitch of a set of Allen Edmonds men’s boots, something I’ve learned through personal experience over the years. I’ve found the American company makes boots and dress shoes with supple-yet-strong leather, the kind that develops a rich patina over time.

These boots also mold to your foot all the while through Goodyear welted craftsmanship. Sounds too good to be true (as well as mighty impressive), right? Well, you best believe it, which brings us to the positively stunning Allen Edmonds Higgins Mill Boots you see before you today.

They’re crafted from materials like rich Chromexcel leather (at least, that’s the case for the pair shown above), and the timeless lace-up style boasts a versatile rounded toe shape that pairs up nicely with blue jeans or stretch chinos in equal measure.

Allen Edmonds men's boots review.

The Allen Edmonds Higgins Mill Boots aren’t merely a stylish fall footwear choice, though — they boast plenty of functionality, from a custom cork insole (one that molds to your foot) to a weatherproof design from toe to heel. The Allen Edmonds Higgins Mill Boots rest on Dainite rubber soles for added traction and a smooth ride underfoot.

Plus, the 757 last — although a fairly recent introduction to the brand dating back to 2016 — boasts a classic design inspired by vintage logging boots. If you ask me, no matter the shade of handsome leather you select, well, the Allen Edmonds Higgins Mill Boots might just be the most versatile, most dependable fall boots in your rotation right now. Lace ’em up and see for yourself.

Style Pick of the Week: Wolverine 1000 Mile Plain Toe Rugged Boots – A Superb Fall Style Move

Wolverine 1000 Mile Boots review.

It can be difficult, as we discuss often, to improve upon a classic like a pair of the best boots for men — and in my experience, the famed Wolverine 1000 Mile lineup of boots certainly fits the bill in that regard. I’ve been wearing Wolverine 1000 Mile men’s boots for more than a decade now — dating back to my college days in Michigan — and the Western Michigan brand still delivers in matters of quality, craftsmanship and superb style.

That also holds true with the new Wolverine 1000 Mile Rugged Boots, a standout fall style move that manages to improve upon a classic in a major way. Granted, the Wolverine 1000 Mile lineup of boots is already plenty tough to beat, with hard-wearing construction, classic good looks and some of the finest bootmaking processes stitched into every pair.

And yet, the Wolverine 1000 Mile Rugged Boots amp things up in a few key ways — all the better to lace up a pair with your favorite selvedge jeans or canvas work pants as you take on a fall weekend cabin getaway (to name but one seasonal pursuit). The Wolverine 1000 Mile Rugged Boots feature resoleable Goodyear welt construction for long-lasting quality and durability, and that construction is accented by a rugged, treaded Vibram outsole.

Wolverine 1000 Mile men's boots review.

The Wolverine 1000 Mile Rugged Boots are also built with truly exceptional Horween leather from Chicago, and then handcrafted with plenty of care. It’s a difference you can feel in every pair of the Wolverine 1000 Mile Rugged Boots, at least in my experience with the brand.

And these boots, although they rest on a different outsole, still share the same pedigree and toughness that’s made the 1000 Mile line a favorite since 1914 — yes, 1914! That’s a long legacy of delivering some of the best men’s boots, my friends.

With Wolverine, and with the Wolverine 1000 Mile Rugged Boots — which should age handsomely and patina nicely with every wear — you can be absolutely sure you’re investing in quality, versatility and timeless appeal. ‘Tis the season to find your new favorite boots.

Style Pick of the Week: Wolverine x Old Rip Van Winkle 1000 Mile Boots – A New Must-Have Pair of Boots for Fall

Wolverine 1000 Mile Boots review.

Whenever I come across a standout pair of rugged leather boots, I tend to pay close attention — and few pairs of boots catch my eye quite like those that hail from Michigan’s own Wolverine, a famed work boot company with a penchant for performance, durability and handsome appeal.

Yes indeed, they make some of the best boots for men on the market, and the new Wolverine x Old Rip Van Winkle 1000 Mile Boots live up to that pedigree quite nicely. These stylish wedge sole men’s boots mark the fourth collaboration between the iconic bourbon company and the famed bootmaker, and they’ve got all the hallmarks of your new favorite pair of boots.

Wolverine x Old Rip Van Winkle boots.

As the company notes, the Wolverine x Old Rip Van Winkle 1000 Mile Boots were “inspired by the rich caramel and wood notes of Old Rip Van Winkle 10 Year,” with rugged good looks and style points to match.

This particular pair builds off the famed 1000 Mile silhouette, and uses luxe leather in a distinctly bourbon-esque shade. Of course, the brand notes that they’ll “develop a patina and a
unique character with time,” and that makes them more than worth the surprisingly agreeable $249 price tag.

A hand-numbered, woven label on the tongue sets apart each pair of the Wolverine x Old Rip Van Winkle 1000 Mile Boots, which are also finished off with vintage-inspired hardware and contrast stitching for plenty of style points.

As with other pairs of my favorite Wolverine leather boots, the Wolverine x Old Rip Van Winkle 1000 Mile Boots team stylishly with your go-to, expertly faded blue jeans or with tobacco-hued stretch chinos, for instance.

And just like legendary Pappy Van Winkle bourbon, the Wolverine x Old Rip Van Winkle 1000 Mile Boots are built to stand the test of time — do yourself a favor and join me in securing your set of these must-have men’s boots for fall, my friends.