The Sunday Sale: The Huckberry Annual Winter Sale Boasts Stylish Savings on the Gear Of Your Dreams

Huckberry Annual Winter Sale 2026.

When the going gets tough and winter waits at your doorstep, I’d wager it’s high time to gear up and get out there, rather than shy away from the snow. At least, that’s what my good friends at Huckberry tend to do, with an assortment of the best gear for men and the toughest layers, most stylish sweaters and classically cool pants, henleys, accessories and more — much, much more, of course.

In fact, that list barely scratches the surface, as the company stocks and sells just about everything you need for your next winter #OOTD — a fact you very well know if you keep up with the digital pages of this Brooklyn menswear blog. From handsome leather boots to expertly cut corduroy pants, all-American selvedge denim and an eye-catching assortment of watches and goods for your everyday carry, yes indeed, Huckberry just about has it all.

And it’s your lucky day, in fact, since the Huckberry Annual Winter Sale serves up tremendous savings aplenty on a vast assortment of the best menswear for winter (and beyond). From rugged and road-ready Huckberry x Danner boots to utterly classic Flint and Tinder corduroy pants, there are timeless and easily wearable finds aplenty — as well as some hidden gems in the mix that aren’t normally for sale.

For instance, take the rare, fashionable and performance-minded throwback nature of the Huckberry x Timex 1979 Black Max Watch — a gem of a timepiece that’s selling quickly and seriously built to last. There’s also a full selection of timeless outdoor gear from the fan-favorite retailer, including cozy Relwen puffer jackets, handsome sweaters with a vintage look and feel, and a stylish range of leather boots, many with durable Vibram construction.

An assortment of Huckberry’s rugged waxed jackets also get the axe in terms of discounts — to say there’s something for everyone within the hallowed halls of the Huckberry Annual Winter Sale is an understatement, my friends — make haste!

You won’t find discounts quite like those up for grabs at the Huckberry Annual Winter Sale for very long: This eye-catching and envy-inducing sale runs online only at Huckberry through February 8th, my friends.

What do you have your eye on? Again, there’s gear for every sense of style and adventure at Huckberry — look no further than one of the best online shops for men, indeed. Cheers, and we’ll see you out there.

See Now, Buy Now: These Proof Rover Work Pants from Huckberry are Ready for Winter’s Worst

Best work pants for men.

If your neck of the woods looks anything like mine these days, I’m willing to bet you’re dealing with your fair share of frigid wind, deep snow and foul conditions aplenty. And yet, the work doesn’t stop, be it your winter to-do list or the ever-mounting need to shovel snow, dig yourself out and perhaps get back to the office.

For whatever’s in your way and whatever happens to be on your to-do list, the best workwear can handle it all — and then some. The best work pants for men, while not traditional snow pants you’d wear on a mountain, are more than equipped to take on the task at hand, especially if the sturdy work pants for men are the Proof Rover Double Knee Work Pants, which blend form and function in a reliably rugged way from the good folks at Huckberry. Better still is the fact that you can save 15 percent on your purchase of two pairs — but let’s dive into why you’d want to do that, shall we?

There’s always much to love in the way of durable winter gear, performance-minded menswear and tough-as-nails supplies in the digital shelves at Huckberry, and the road-ready Proof Rover Double Knee Work Pants should more than pass muster. Proof delivers adventure-minded performance menswear under the Huckberry umbrella, from its famed 72-Hour Merino T-Shirts (truly worn for three days of hard-working off-grid excursions) to the fan-favorite Proof Rover Pants, which my Proof reviews have covered here on this Brooklyn style blog.

Best work pants for men.

The hard-working Proof Rover Double Knee Work Pants share much of the same DNA as the flagship Proof Rover Pants, starting with their fabrication. Your new favorite winter pants feature a tough-as-can-be cotton-blend, recycled poly fabric construction that regulates your temperature, boasts just enough useful stretch and wicks away moisture at the same time. Talk about a laundry list of features designed to move with you and make tackling your to-do list all that much easier.

Lest we forget, the Proof Rover Double Knee Work Pants feature reinforced construction at key stress points through the thigh and knee, plus riveted pockets for an ultra-sturdy finish. In my experience wearing the Proof Rover Pants, the pigment-dye finish makes these rugged work pants for men surprisingly sturdy and yet supple out of the box, all the better to mold to your body over time.

Of course, whether layered up with a thermal henley and a wool-lined waxed trucker jacket or styled with a burly crewneck sweater and a barn coat, the dependable Proof Rover Double Knee Work Pants should move easily with you, thanks to the gusseted crotch. Huckberry even built out the forward-thinking Proof Rover Double Knee Work Pants with a back waistband pocket for your everyday carry.

Rounding things out is the fact that some of the best men’s work pants come in three proprietary Huckberry fits, including an Athletic Tapered fit (my personal favorite) and a crisp Slim fit — not to fear though, as the reliable Proof Rover Double Knee Work Pants should still readily team with pull-on work boots or Red Wing Iron Ranger Boots. Don’t delay snapping up your new go-to work pants — they can handle winter’s worst, and then some.

The Thursday Buy: Flint and Tinder Just Teamed Up With Rancourt & Co. On Some Seriously Rugged New Boots

Flint and Tinder x Rancourt & Co.

We’re back after a brief hiatus and my latest style and spirits-focused jaunt across the pond, as you might have seen on my Instagram, so let’s get into it today, my friends. In matters of the best winter style essentials, it can sometimes feel like you’ve seen it all — how much better can a pair of rugged winter boots get, after all? Well, in the case of the good folks at Huckberry, a line has been drawn in the sand, or rather, the ante has been upped even further with the iconic modern retailer’s latest standout footwear collaboration.

Again, that’s a high bar to clear considering the likes of Huckberry x Danner have hit the brand’s digital shelves in recent years, but Flint and Tinder x Rancourt & Co. delivers the goods once again, and then some. If you’ve read this Brooklyn style blog or perused the Huckberry site as of late, you’ll know that Flint and Tinder menswear is Americana through and through, inspired by the open road, the American West and the great outdoors.

Best chukka boots for men.

That lineup includes one of the best waxed trucker jackets on the market, plus expertly faded denim and crisp chinos abound, along with perfectly crafted footwear, like the Flint and Tinder x Rancourt & Co. Acadia Chukka Boots (among other F&T offerings, of course). The just-launched, highly durable and seriously rugged Flint and Tinder x Rancourt & Co. Acadia Chukka Boots meet the high standards of both Huckberry and Rancourt & Co., the generational Maine-based footwear maker known for serious attention to craft and handsewn, eye-catching and heirloom-quality boots and moccasins.

It’s a family business run the right way, to say the very least, and that lends itself to some iconic and hard-wearing boots and shoes. The Flint and Tinder x Rancourt & Co. Acadia Chukka Boots are the latest in that long line of enviable boots and shoes, including high-top sneakers that sold out quickly more than a decade ago.

So if you want a piece of the latest and greatest American-made boots for men, take heed:Your new favorite boots won’t be around for very long.

The Flint and Tinder x Rancourt & Co. Acadia Chukka Boots boast Chicago-sourced pull-up bison leather with rich texture made to take on a handsome patina over time.

These stylish men’s leather boots are built atop a Reltex Ranger outsole that should prove lightweight and yet traction-minded, while the Flint and Tinder x Rancourt & Co. Acadia Chukka Boots are unlined — grab a pair of your favorite boot socks, cuff your flannel-lined denim and get out there to take on the winter cold. Select sizes are selling fast, so now is as grand a time as any to upgrade your winter boot game.

The Sunday Sale: These Rugged Workwear Boots from Huckberry are the Discounted Footwear Move Your Closet Needs

As we step assuredly into the winter season and the new year, I’d wager that the right pair of rugged leather boots for men can, in some cases, make all the difference in matters of form and function. Throw in a pair that’s tried-and-true, tested for work as well as serious style points and durability, and you might say we’re cookin’ with gas, as the adage goes.

That’s why I tend to trust the good folks at Huckberry, keen observers of the best winter menswear and keen sellers of durable, Americana-inspired and utterly classic men’s style all around.

And so it goes with today’s on-sale pick, a barnburner of a discount from the Huckberry Sale section revolving around the Rhodes Footwear Work Wedge Chelsea Boots.

As at home on the shop floor or near the drafting table as they are seated at your favorite bar stool beneath the cuff of a perfect pair of indigo jeans, these stylish Chelsea boots for men excel at both work and play, quite literally — and they’re on sale right now in the Huckberry Sale section, my friends.

Best Chelsea boots for men.

Rugged gear made for the moment at hand is always a treat to find at a bargain (the Rhodes Footwear Work Wedge Chelsea Boots are marked down to $211 from $248), and these tough work Chelsea boots pack in a laundry list of features along with their traditional workwear good looks.

The Rhodes Footwear Work Wedge Chelsea Boots boast textured full-grain leather uppers constructed in Leon, Mexico, a place known for its fine footwear craftsmanship.

The lightweight Meramec PU outsole, on the other hand, offers grip, rebound, comfort and support, while you’ll note that these boots feature reinforced leather in key stress spots (like the top of the vamp, where the heel meets the shaft of the boot — the details make the difference, my friends!).

Dual pull tabs offer an easy-on, easy-off wearing experience, as do the elastic side gores — these are tough-as-nails Chelsea boots as fit for wearing with canvas work pants and a henley-plus-waxed trucker jacket as they are with a light wash denim shirt and dark indigo blue jeans for casually contrasting, off-duty style. You might not get all that many chances to score a pair of the best Chelsea boots for men like the Rhodes Footwear Work Wedge Chelsea Boots, so I’d urge you to jump at the chance — happy shopping, my friends.

Style Pick of the Week: Flint and Tinder Sherpa-Lined Winter Gloves – A Must-Buy Winter Style Accessory

Best winter gloves for men.

As winter’s worst weather bears down, it’s mighty beneficial to take stock in advance of the gear in your rotation — staple items like a durable winter parka or a cozy thermal henley are going to go a long, long way indeed, but don’t forget the everyday carry essentials that make it all possible as far as stylish winter adventures are concerned.

The great news is, these selections needn’t be an afterthought, and they needn’t forgo dashing good looks for the sake of winter weather-minded performance — the best winter gloves for men certainly qualify in this regard, my friends, and you can find them at one of your favorite online menswear stores: I’m talking, of course, about the good folks at Huckberry.

And in much the same way as they make a highly rugged, hard-wearing waxed trucker jacket or a do-it-all flannel shirt, Flint and Tinder delivers the goods as far as the best gloves for men are concerned.

The details really do make the difference, and if ever you’ve stepped foot in a winter storm without a proper pair of gloves to accompany you, then I’m willing to bet you’ve learned your lesson. The Flint and Tinder Sherpa-Lined Leather Gloves, on the other hand, defy convention and deliver rugged performance, warmth and style in one complete package.

You see, the Flint and Tinder Sherpa-Lined Leather Gloves strike the ideal balance between too bulky and too sleek — the right balance that makes them rugged and durable enough to wear alongside a trucker jacket or a flannel shirt jacket, or else with a crispy navy topcoat as a complementary piece alongside your best winter wool suit.

The Flint and Tinder Sherpa-Lined Leather Gloves blend durable 100 percent textured leather (available in versatile shades like Cognac, Bourbon or razor-sharp Black) with a cozy sherpa lining for the utmost in winter warmth.

The Flint and Tinder script font at the cuff is a stylish touch that helps these Huckberry-approved gloves stand out in a fashionable manner, while the Flint and Tinder Sherpa-Lined Leather Gloves also happen to be on sale (you can scoop up your own pair at Huckberry now for less than $75).

Sizes are going quickly as far as the Flint and Tinder Sherpa-Lined Leather Gloves are concerned, and it’s not hard to see why: Durability, style points aplenty and exceptional winter warmth are the name of the game this season, so scoop up a pair of the finest men’s winter gloves on the market — your digits will assuredly thank you.

The Sunday Sale: This Flint and Tinder Midweight Flannel Is One Stellar Pick from The Huckberry ‘See You Out There’ Sale

Best flannel shirts for men.

The holidays — and that period between Christmas and New Year’s — come but once a year, but thankfully, the chance to shop menswear essentials from Huckberry’s ever-growing sale section is a bit more frequent.

At least, that’s the case for the next few days as Huckberry puts on its See You Out There Sale, which celebrates the promise of stylish adventures heading into the new year, all by offering up discounts on underrated yet buzzy menswear and gear for the modern fellow.

The See You Out There Sale serves up savings of up to 45% off, a standout deal considering plenty of picks from Huckberry-approved retailers can prove a bit pricey at times. Case in point: The selection for this year’s must-shop winter fashion sale includes normally pricey offerings from the likes of Wax London, Freenote Cloth, Barbour and Kestin — all brands worth a pretty penny normally, but each worth your hard-earned cash right now.

And yet, the See You Out There Sale also features classic in-house picks from Huckberry, like the handsome and durable Flint and Tinder Cozy Midweight Flannel Shirt shown at the top of the page — what’s not to love about that, ehh?

If you keep up with this Brooklyn style blog, you know Flint and Tinder for its slew of modern icons, including its waxed trucker jackets, its everyday-approved 365 Pants, its shirt jackets and heritage cardigans, and even its thick-knit, anything-goes T-shirts.

So now that you can score a durable, rugged and easy-to-layer winter style move like the Flint and Tinder Cozy Midweight Flannel Shirt — while supplies last, of course — I’d say this latest Huckberry sale is sort of like the perfect storm. Everything lines up (nicely, in this case), and just in time for casually laidback seasonal layering and style points aplenty.

Made with a reliable crossback yoke for ease of movement and finished with two button-chest pockets for shirt jacket-esque layering potential, count this soft-yet-sturdy flannel shirt among the very best of the offerings on sale until January 1st at the See You Out There Sale.

Triple-needle stitching lends durability, while the Umber Plaid color is perfectly well-suited for pairing with light tan chinos, light grey corduroy trousers or indigo blue jeans and a waffle henley (other color combinations are up for grabs at full price, for what it’s worth)..

For under $90, your new favorite flannel shirt is a prime example of what you can unearth when you scour the discounts on hand at the See You Out There Sale — a sale that shines a spotlight on the unexpected, but for a limited time only. Load up your (digital) shopping cart accordingly, folks.

The Thursday Buy: This USA-Made Huckberry Beanie Is One of the Best Christmas Gifts Under $50 For Men

Best beanie cap for men.

If your schedule looks anything like mine these days, as the year somehow winds down at a sprint’s pace, then your time is probably quite limited, yes? As in, at this point, a week before Christmas, you very well might be looking for some last-minute style and gifting inspiration — and in quick succession, at that.

Well, have no fear, because Huckberry is here to save the day with one of the best men’s gifts under $50, one you’ve still got time to order just before Christmas — just in the (saint) nick of time, one might say.

Ever a reliable outlet for some of the best gifts for men, period, from sturdy waxed trucker jackets to handsome leather boots, outdoor-inspired whiskey decanters, sturdy pocket knives, essential books and cozy accessories, the Huckberry Christmas 2025 Gift Guide is a true wonder to behold.

And in addition to big-ticket items, it’s also packed with hidden gems aplenty, like the Huckberry Made in USA Watch Cap Beanie. If you’ve reached the point in your search for the best men’s gifts where it now feels like crunch time, then this number is what you’re going to want to buy ASAP; let’s make it easy on ourselves, ehh?

The Huckberry Made in USA Watch Cap Beanie offers much to love as a stocking stuffer, as a gift for that tough-to-buy-for brother-in-law, or as a solution to what to get your outdoorsy father or father-in-law at a moment’s notice. It’s far from any old beanie cap, taking inspiration from naval watch caps and using a thick-knit, snug construction with a large cuffed design for maximum coverage.

The Huckberry Made in USA Watch Cap Beanie comes in a range of colors to suit every taste, and the small Huckberry logo patch is tasteful and subtle rather than overly large (the logo size on one of the best beanie caps can sometimes be a deal breaker in matters of style, can it not?).

The great thing about this USA-made beanie is its mix of versatility in looks — a black beanie cap goes with darn near everything, does it not? — plus its highly affordable price tag.

Heck, pick up three or four if you want the fellas in your family (yourself included, perhaps?) to look cozy, dapper and casually rugged all at once. If the time has come to expedite your gifting search with affordability in mind, you’ve come to the right place for the Huckberry Made in USA Watch Cap Beanie.

See Now, Buy Now: This Handsome Leather Duffle Bag from Unmarked and Huckberry Is Perfect for All Your Winter Travel

For as much as we talk about the best men’s style essentials and top gear for the modern man, it’s worth putting just as much care and thought into how you ensure those essentials stay in top-notch shape and perform their very best from point A to point B.

So, rather than hauling your favorite leather boots and one of the best chambray shirts –among other holiday style must-haves — in just any old bag, why not level up a touch this season with one of the best weekender bags for men?

Add in the fact that it’s sourced and sold by one of your favorite online retailers — the good folks at Huckberry — and we’re looking at a certified winner when it comes to some of the best travel gear for guys.

And as a matter of fact, there’s a great reason the Unmarked Leather Weekender Bag is even listed among Huckberry’s Gifts for the Guy Who Has It All — it’s just that cool, stylish, dependable and forward-thinking in matters of craft and heritage. How about that, ehh? And if you — or the impossible-to-shop-for guy on your list — hasn’t heard from Unmarked, holiday gifting can present a prime opportunity to either refresh your own leather goods rotation or help a trusted, stylish fellow in your life level things up considerably.

The Unmarked Leather Weekender Bag sold by Huckberry features a rich Shedron shade of leather in an exclusive Western pattern that’s all the rage (making it worth its price tag of $400, in my experience — not a bad deal for a weekender bag you can reliably take across the country and globe as it develops better patina with age. The Unmarked Leather Weekender Bag boasts glazed pull-up tanned leather and vegetable-tanned strips for ornate detailing and richly crafted, rugged quality — its brass hardware is made in America, while the hard-working yet stylish Unmarked Leather Weekender Bag features reinforced rivets and a gold-tone brass zipper.

And another thing: Because you’re perhaps wondering what exactly you can fit in the Unmarked Leather Weekender Bag, note that its dimensions clock in at 17” x 11½” x 9”. That should give you enough space for a weekend away, and perhaps even enough space to pack a durable pair of Unmarked’s impeccably designed leather boots.

For the guy who values traveling in style, with goods built to last (even if you just score it for yourself!), this fashionable leather weekender bag is the right move.

Style Pick of the Week: Huckberry x Timex Black Max Watch – A Rare and Rugged Wrist Game Upgrade

Huckberry x Timex review.

I’m often on the lookout for the latest and greatest gear, from the coolest new men’s watches to the right pair of leather boots or the perfect henley — or some combination of all of the above, which can readily be worn at the same time (as you well know if you keep up with this blog!).

And so when two respected brands I love come together to craft a rugged watch, you could call it a perfect meeting of the minds, one that makes so much sense, it’s enough to keep you coming back for more — and so it goes with Huckberry x Timex, an ongoing partnership that’s resulted in some highly rugged, hard-wearing watches with plenty of style points.

The latest in the Huckberry x Timex series is no slouch either, to say the very least. The Huckberry x Timex 1979 Black Max, which just debuted yesterday, in fact, takes things to the next level in terms of Huckberry’s penchant for rugged and durable gear, combined with the Timex knack for using historical inspiration to craft wildly useful modern watches.

Available for a limited time only, the Huckberry x Timex 1979 Black Max harkens back to the 1970s and racing watches of the era, bringing back what the famed American watchmaker calls one of its most sought-after vintage collectibles. The meeting of the minds simply couldn’t be more perfect, at least in my book, featuring a bold racing dial and a blacked-out titanium case for plenty of durability.

The Huckberry x Timex 1979 Black Max also features what looks to be a matte-finish stainless steel band to complement its hard-wearing 41mm case. And within, you’ll find a reliable quartz movement, while the crown itself features the Huckberry logo.

It’s yet another sturdy watch from a brand well-known for crafting ’em the right way, and at highly affordable prices, to boot. It’s also priced to sell at just $249, making the new Huckberry x Timex 1979 Black Max a worthy addition to your shopping cart (and your everyday carry) this holiday season.

It’s also suited for adventures off-grid, boasting 100 meters of water resistance — all in a strong, dependable Huckberry-approved design. If I had to guess, I’d say your new favorite adventure watch just might have arrived.

See Now, Buy Now: These Flint and Tinder Corduroy Pants are Your New Favorite Style Essential this Season

Best corduroy pants for men.

Perhaps you’ve noticed that as the temperature plummets even further, you need something a little more sturdy in every element of your wardrobe. That goes for your trusty parka as well as your thick-knit flannel shirt and dependable fisherman sweater or shawl cardigan (all of which we’ve covered here on the blog in recent weeks and months!), but what about your rotation of the best pants for men?

While rugged blue jeans and even dressy wool suit trousers and crisp chinos all have their place in your style rotation, it’s sometimes ideal to lean into the charms of the season in terms of texture and style — and that’s where the good folks at Huckberry can help, a fact you well know if you’ve read this Brooklyn men’s style blog from time to time.

Let’s get more specific when it comes to texture and rich craftsmanship: Look to the folks at Flint and Tinder, well-known for the lightweight, effortless dependability of the Flint and Tinder 365 Pants, to effectively winterize your options in terms of the best men’s pants, period.

You see, the best corduroy pants for men toe the line between distinction and dressy appeal, and the versatility that every guy needs — especially when they come in a design that closely mirrors your go-to five-pocket blue jeans or chinos. And the Flint and Tinder Corduroy 365 Pants toe that line in crisply cut, stylish, seriously cool fashion — gone are the days of stuffy corduroy pants worn in years past, replaced instead by a handsome tailored cut, rich color options and simply excellent fabric.

Available in fits ranging from Huckberry’s proprietary HB Straight or HB Athletic Tapered, the sharp-as-can-be Flint and Tinder Corduroy 365 Pants are your perfect go-between when you want a classier look than casually rugged blue jeans, but want to avoid going as formal as suit trousers.

Best corduroy pants for men.

The Flint and Tinder Corduroy 365 Pants boast what Huckberry calls “the perfect amount of stretch,” even featuring a slight taper to the leg in the Straight-cut variety for a clean look and feel. And the five-pocket design is reliable and timeless — as easy to wear with a thermal henley and a chambray shirt as with a wool blazer and a stretch dress shirt.

The Flint and Tinder Corduroy 365 Pants come in four fashionable colors (including my personal favorite, Whiskey, plus the wear-with-anything Taupe and the eye-catching olive hue of Moss). And with garment-dyed fabric, the right amount of stretch and the crisp fit you can count on from the good folks at Huckberry, it might just be a surefire bet that these stylish men’s corduroy pants are the perfect step up from your trusted blue jeans this holiday season (and well beyond).