Style Pick of the Week: Sanders Hi-Top Chukka Boots – A Luxe Fall Footwear Upgrade

Best chukka boots for men.

There are plentiful welcome signs as far as the return of fall is concerned: The pleasant crunch of leaves underfoot, a brisk breeze carried on the air, the welcome cracking of a cold can of Oktoberfest beer and of course, the return of plentiful opportunities to wear your new favorite boots. Or rather, your old favorite boots.

Or a dash of both, and that’s where a refresh when it comes to the best chukka boots for men can sort out your footwear rotation in fine form.

Naturally, we turn towards Huckberry for a selection of the best boots for men — and I’ve got even better news. The fan-favorite Sanders Hi-Top Chukka Boots, a modern offering from a heritage British brand, are back and better than ever. Newly restocked, the Sanders Hi-Top Chukka Boots are billed by Huckberry as “British-made chukkas for shoe connoisseurs,” with hand-finishing processes and exceptional craftsmanship dating back to the 1870s.

Best suede chukka boots for men.

These handsome chukka boots are made all the better by soft, supple leather lining accented by an elegant suede upper. And with a refined toe shape and a chunky, eye-catching and utterly comfortable outsole, these are the sort of stylish men’s chukka boots you can wear with wool trousers and a navy blazer as readily as you can style them with dark blue jeans and a trim flannel shirt.

The rubber crepe outsole on the Sanders Hi-Top Chukka Boots is a major selling point: That outsole should deliver comfort, rebound and even a touch of traction (although careful about getting these suede chukka boots wet, my friends).

In a rich shade of brown, the Sanders Hi-Top Chukka Boots are especially appealing and stylish when worn with everything from olive chinos to burgundy corduroy trousers and even faded mid-wash denim (it’s helpful that you can certainly find many a complementary piece at Huckberry to go with your new favorite pair of fall boots).

With made-in-England construction and an ankle-length cut accented by a minimal two-eyelet design, the Sanders Hi-Top Chukka Boots can be dressed up or dressed down (somewhat) with ease.

And while $310 might seem a pretty penny to pay for chukka boots, these are some of the best-made and most versatile boots for men on the market, at least in my experience. Time to lace up and get out there, my friends.

The Tuesday Steal: These Rugged Hybrid Chelsea Boots from Huckberry & LUCA Belong In Your Closet

Best Chelsea boots for men.

Stepping from one season into the next can sometimes start, quite literally, with the proper first step as far as your footwear rotation is concerned — among a host of #menswear essentials, that is. And for bridging the gap between the end of August and the start of fall, I’d wager that a pair of the best Chelsea boots for men get the job done handsomely, especially a pair as designed and sold by the good folks at Huckberry. Yes indeed, for what lies ahead, the durable, rugged LUCA Terra Slip On Chelsea Sneaker Boots could be your best bet. Scroll on for more, my friends.

Save the heavy-duty work or snow boots for when temperatures really plummet — instead, opt for a pair with a hybrid design and rugged utility, like the LUCA Terra Slip On Chelsea Sneaker Boots. They’re the best of both worlds, they’re designed and sold by a standout in-house brand at Huckberry, and they’re on sale right now — how can it get better than that? Let’s count the ways, my friends.

The hard-working, hard-wearing LUCA Terra Slip On Chelsea Sneaker Boots do exactly as they say, blending the supple nature of a full-grain leather or suede Italian upper with a cupsole sneaker outsole for plenty of springy rebound and comfort.

The LUCA Terra Slip On Chelsea Sneaker Boots also boast cushioned removable insoles and a leather lining that should mold to your foot over time, whether you wear these handsome leather sneaker boots with expertly faded blue jeans, with olive chinos or with grey canvas work pants.

The LUCA Terra Slip On Chelsea Sneaker Boots also feature front and back pull tabs for easy-on, easy-off access, while the cupsole base contrasts nicely with the leather upper. Huckberry notes these pull-on boots feature a versatile silhouette made to be worn with a variety of outfits — I’d even go so far as to wear these with dark blue jeans, a light blue chambray shirt and a navy stretch cotton blazer for a mix of high-low, business casual style.

It doesn’t hurt that the LUCA Terra Slip On Chelsea Sneaker Boots are on sale right now through Huckberry in sizes up to 13 and in four crisp, easy-to-style combinations of leather or suede. With supreme comfort top of mind and a polished silhouette you can dress up or dress down, these could just be the most dependable boots in your early fall footwear rotation — take the LUCA Terra Slip On Chelsea Sneaker Boots for a spin and let me know how they treat you.

The Thursday Buy: Lace Up these Rugged Danner Logger Moc Boots from Huckberry for Every Fall Pursuit

Danner men's boots review.

As we inch ever closer to Labor Day weekend and the unofficial closing round of summer, what menswear and gear picks have been on your mind (and perhaps, in your digital shopping cart)? Slightly cooler days and nights lend themselves to preparing for a new season — the right way, as we so often talk about on this Brooklyn style blog.

Naturally, I’ve found the best gear and menswear tends to come from Huckberry, the Americana and adventure retailer that has a penchant for stocking some of the most stylish selections on the market from a host of brands.

That list certainly includes the good folks at Pacific Northwest footwear maker Danner, a heritage brand that’s taken a modern turn (and not for the worse!) in recent decades.

They’ve carefully curated their lineup to include lightweight hiking boots, tactical boots, handsome leather lifestyle boots and rugged leather boots for men that fall somewhere in between all three of those categories, which is all the better if you love shopping the best boots for men.

And among that crop, the Danner Logger Moc 917 GTX fits the bill quite nicely indeed in terms of rugged throwback good looks and modern performance. The Danner Logger Moc 917 GTX boasts all the hallmarks of classic Danner boots, harkening back to the days when the Portland-based company first made boots for loggers in the 1930s using… you guessed it, GORE-TEX fabrication.

The Danner Logger Moc 917 GTX carries on that lineage in handsome fashion, using a sturdy, thick yet supple leather upper bolstered by a waterproof and breathable GORE-TEX liner. The impressive combination rests atop its namesake Vibram 917 outsole, boasting a small lug rubber outsole design for traction and a wedge sole with added support at the heel.

The two-tone design of the Danner Logger Moc 917 GTX is a handsome touch, particularly when the brand uses contrast stitching across the moccasin upper. In my experience, boots like the Danner Logger Moc 917 GTX tend to wear well with durable classics, like indigo blue selvedge or perhaps light olive chinos or slate grey canvas work pants.

And you can certainly style the Danner Logger Moc 917 GTX in off-duty fashion, but the waterproof and breathable GORE-TEX construction in the liner means you can take these boots off-trail and out into the field if need be.

Complete with tonal laces to match the lower part of the moccasin upper, every detail has been properly thought out as far as the newly iconic, ultra-comfortable and assuredly hard-wearing Danner Logger Moc 917 GTX is concerned. Slip into a pair this fall season and let me know how they treat you.

The Sunday Sale: Bespoke Post Is Now Offering a Discount on these Rugged SeaVees Sierra Adventure Boots

Best sneaker boots for men.

Stepping from one season from the next — from late summer into very early fall — is often as simple as making your transition from the ground up.

So while items like classic blue jeans and a sturdy henley are men’s style essentials well-suited for multiple seasons, it’s sometimes a wise move to work a pair of rugged leather boots (or in this case, stylish sneaker boots) back into your rotation slowly but surely — as summer wanes and fall approaches, of course. And there might not be a pair of men’s sneaker boots as well suited for the moment at hand as the SeaVees Sierra Adventure Boots.

As you might recall if you read this Brooklyn style blog frequently, Bespoke Post and SeaVees teamed up on the perfect pair of men’s winter boots at the end of 2023 – as luck would have it, select pairs of the handsome SeaVees Sierra Adventure Boots are still up for grabs as summer draws to a close.

The SeaVees Sierra Adventure Boots are now 50 percent off, with sizes going fast in two exclusive Bespoke Post colorways, designs that the upstart NYC retailer says were “inspired by the SeaVees ‘60s-era “California cool,” reflecting the shared commitment to quality and innovation from both companies.

The result? An on-sale pair of rugged, adventure-ready footwear that starts with a durable oiled leather upper blended with water-resistant Ventile cotton canvas. The SeaVees Sierra Adventure Boots also boast a hard-wearing natural rubber lug outsole for maximum traction on hiking trails, rocky coastline and dewy fall morning grass, while eye-catching touches like rawhide leather laces finish off the dependable SeaVees Sierra Adventure Boots in stylish fashion.

The design takes its cues from SeaVees’ popular Mammoth and Mariner Boots, but features touches exclusive to Bespoke Post, including an embossed heel logo. With an ankle-high design and sturdy construction, these hard-working boots are well-suited for everything from late summer yard work to early fall tailgates and brewery beers.

And for 50 percent off right now, it’s almost an imperative that you score a pair of the SeaVees Sierra Adventure Boots while they’re still around (although take heed, since sizes are rolling away quickly). Welcome the season at hand from the ground up, as we’ve said, and you’ll be more ready for fall than ever before.

Style Pick of the Week: Wolverine 1000 Mile Rugged Leather Boots – Durable Adventure Boots for Spring (And Beyond)

There’s a sort of spring cleaning “style to-do” list of sorts when it comes to revamping and refreshing your wardrobe for the season at hand, starting from the ground up (at least, in my experience).

When you start out a seasonal refresh by looking at your footwear rotation — what to keep from the fall and winter months, what to bring back for spring and what to shelve entirely — perhaps you focus on an assortment of the best men’s boots — guilty as charged. In fact, you’ll often find me wearing a pair of the best leather boots from a company like Wolverine, based in my home state of Michigan and a longtime favorite of mine when it comes to the best boot brands for men.

Its roster includes boots legendary for their toughness, especially the Wolverine 1000 Mile lineup, and that lineup gets even better — with a bit of multi-season functionality in the mix via the Wolverine 1000 Mile Plain Toe Rugged Boots. You can certainly head elsewhere here on the blog to read more Wolverine boot reviews, but let’s dive into what makes these similar — and different from! — other classic Wolverine 1000 Mile men’s boots.

Wolverine 1000 Mile boots review.

The Wolverine 1000 Mile Plain Toe Rugged Boots retain many of the classic features that make the original Wolverine 1000 Mile men’s boots such a fan favorite and a success, including decades of bootmaking heritage. They’re made based on an archival work boot last pattern, then fashioned with famously tough Horween leather out of Chicago — a true Midwest style collaboration.

These handsome leather boots (available in the rich Brown seen here as well as an edgy Black edition) are then updated with a rugged Vibram outsole featuring thick treads for optimal traction on slick city streets this spring (and beyond, of course).

The Wolverine 1000 Mile Plain Toe Rugged Boots are also fashioned with Goodyear welt construction, that way they can be resoled for years of wear — and at the price point (an investment at nearly $400), you’ll want to get as much wear as you can out of the casually rugged yet highly functional Wolverine 1000 Mile Plain Toe Rugged Boots.

The western Michigan-based company, also known for its work boots of all shades, shapes and sizes, calls the Wolverine 1000 Mile Plain Toe Rugged Boots “ruggedly refined,” and I’d say they’re right on the money. The silhouette is able to be paired seamlessly with indigo jeans, black denim or even olive chinos, then styled classically with a heathered henley and a waxed trucker jacket, to name but one way to get the most out of the Wolverine 1000 Mile Plain Toe Rugged Boots.

With great looks, top-notch construction and a long-lasting build and design, it looks to me like you just might have found your new favorite boots for spring — and beyond.

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.