The Sunday Sale: The Huckberry Annual Winter Sale Boasts Some of the Best Seasonal Deals on Gear and Menswear

Huckberry Annual Winter Sale 2025.

It’s the most wonderful time of the year, my friends. Late January feels a bit unconventional though, with the doldrums of the season upon us, but I’m talking specifically about the chance to shop some of the best gear and menswear from my friends at Huckberry. Yessir, the Huckberry Annual Winter Sale offers up bundles of savings on rugged style essentials, everyday carry gear, durable footwear, tough-as-nails jackets and much more.

There’s a full roster of heavy hitters on sale for as much as 40 percent off, including cashmmere sweaters, sturdy waxed jackets, one particular Japanese Huckberry beanie and even some outstanding pairs of stylish, handsome leather boots. If you ask me, the Huckberry Annual Winter Sale has just about everything you could want in a rotation of winter gear — and selections you can wear long past this season and into the next.

There are selections from trusted Huckberry partner brands like Relwen and Taylor Stitch, plus savings on tried-and-true must-haves from Huckberry in-house purveyors like the legendary craftspeople behind Flint and Tinder. How’s that for savings and style rolled into one? The Huckberry Annual Winter Sale — now through February 6th — is prime time for discounts galore on a standout roster from one of the best online menswear brands, my friends.

Strike while the iron is hot, get your credit card at the ready and make some space in your closet for your favorite menswear essentials — new and old — from the Huckberry Annual Winter Sale, my friends.

Style Pick of the Week: Wills Classic Cashmere Sweater at the Huckberry Annual Winter Sale

Best sweaters for men.

At times, the best style essentials for men are ones that are subtly stylish on the surface, yet even more well-made the deeper you dive in. That certainly holds true for menswear wardrobe selections from Huckberry, a longtime favorite retailer of mine (and yours, if you happen to read this Brooklyn style blog on the regular). Take, for instance, the Wills Classic Cashmere Sweater as shown above.

It’s a straightfoward selection that lives up to its name, and then some, using classic cashmere construction for a luxe finish. That is to say, don’t sleep on it, however.

And while its crewneck design is relatively simple, it’s as easily wearable atop a soft cotton long-sleeve tee as it is with a crisp Oxford shirt.

How’s that for versatility and quality? That doesn’t even take into account the range of neutral, easy-to-style colors in which you’ll find the Wills Classic Cashmere Sweater — and the best part is, it’s also a surprisingly affordable style find that offers wearability seven days a week, from the office to happy hour to date night (and beyond).

The Wills Classic Cashmere Sweater is also billed by Huckberry as boasting the “ideal midweight,” the sort of sweater “you can wear…. no matter the weather.” I see this stylish cashmere sweater for men as being an essential selection in situations more dressy — like a date night, perhaps alongside corduroy trousers — or more casual (as with dark blue denim and rugged leather Chelsea boots from a trusted brand like Ariat).

Better still is the fact that the Wills Classic Cashmere Sweater is on sale right now (marked down below $120) at the Huckberry Annual Winter Sale (more on that on this blog in the days to come).

For now, just know that this sweater is a crisp, essential modern classic that wears well in plenty of style situations — and you’re saving yourself a few bucks in the process as you upgrade your wardrobe, my friends. Cheers to savings and style in spades.

The Thursday Buy: This Flint and Tinder Waxed Jacket is an On-Sale Style Steal at Huckberry

When the going gets tough, when frigid winter weather rolls into town, the truly tough wear Huckberry gear and menswear. At least, that’s what I tend to say, and tend to reach for in my personal wardrobe, and perhaps you’re of the same opinion. That’s what makes it so much fun — yes, fun! — to shop for staple selections like one of the best waxed jackets for men.

And when that particular selection happens to be on sale via the Huckberry Winter Sale right now, that’s all the better, is it not? Yes indeed, the Flint and Tinder Flannel-Lined Quilted Ranch Jacket falls right in line with the San Francisco and Austin-based company’s ethos of rugged Americana and adventure gear.

Even better still is the fact that right now, it’s marked down to below $200. Yes, that’s right: One of the best jackets for men, period, is $200 off — and in a range of sizes and classic colors, like the handsome Charcoal option shown above.

In matters of durability, toughness and style, the Flint and Tinder Flannel-Lined Quilted Ranch Jacket checks all he proper boxes, as one would expect from the famed retailer’s Flint and Tinder line. The Flint and Tinder Flannel-Lined Quilted Ranch Jacket is made in the USA, lending it an extra level of care and attention to detail, while the 10oz. waxed canvas exterior is sturdy, tough and made to get better with age.

Flint and Tinder review.

The Flint and Tinder Flannel-Lined Quilted Ranch Jacket also boasts an ultra-warm flannel lining, while the jacket itself also features 4oz. of insulation for added warmth. It’s a tough-as-nails jacket fit for work or play, from brisk mornings in the fields to nights at the dive bar.

Plus, as our friends at Huckberry note, this jacket features a “re-waxable exterior for a lifetime of water-resistance.” How’s that for a jacket you can depend on for seasons to come? If I were you, I’d scoop up the Flint and Tinder Flannel-Lined Quilted Ranch Jacket as soon as possible.

See Now, Buy Now: The Flint and Tinder Midweight Terry Collection Features Your New Favorite Sweatpants

Best hoodies for men.

In my experience, looking for style staples needn’t be too complicated — or rather, sometimes, you just want a sturdy, reliable, hard-working and yet casual look, perhaps one anchored by one of the best men’s hoodies. It’s a simple sportswear selection made modern when done the right way, as you can see above with the Flint and Tinder Midweight Terry Collection at Huckberry.

The classic hoodie has morphed over the years into a piece that can be casually layered and worn in situations far from the gym. For instance, you can team your new Flint and Tinder hoodie with a rugged waxed trucker jacket, underneath a denim jacket or a field coat, or wear it as a trusty, comfortable all-day travel essential.

Huckberry also recommends styling this reliable new hoodie in classic sportswear fashion, as with joggers and canvas sneakers — weekend coffee runs have never looked so stylish, at least in my experience.

Sturdy loopback cotton gets a garment-washed treatment for softness and comfort right out of the box, while the new Flint and Tinder Midweight Terry Hoodie boasts a durable, dependable design. Features like a double-layer hood and double-layer cuffs see to that sturdiness, while its kangaroo pouch is a staple found on the best hooded sweatshirts for men.

True to form, the Flint and Tinder Midweight Terry Hoodie comes in a range of classic, casual colors, including a sporty shade of heathered grey and even an eye-catching deep green.

Best men's hoodies.

While the Flint and Tinder Midweight Terry Hoodie might seem simple on the surface, it’s built with the kind of durable details that make a big difference when it comes to casual sportswear — made for the gym, the open road and well 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.

Style Pick of the Week: The Flint and Tinder Texas Reserve Collection – Modern, Made-in-America Must-Haves

There’s something to be said for menswear brands that feel modern and of the moment, while at the same time delivering a sense of classic style, the kind that’s rarely ever out of place. Of course, you’ll find those sorts of menswear essentials in spades at fan-favorite Americana-adventure retailer Huckberry, assuredly one of the best online style brands for guys – and a personal favorite.

So when the good folks at Huckberry and Flint and Tinder — the company’s flagship in-house line — put their heads together on a new, made-in-Texas collection, the results are absolutely worth checking out ASAP.

My friends, meet the Flint and Tinder Texas Reserve Collection, a tightly curated, ridiculously well-made trio of Western workwear style picks perfectly suited for the moment at hand.

After all, everything Western seems to be a growing trend in menswear, but Flint and Tinder doesn’t feel like a bandwagon hopper — the brand does things the right way, with quality and rugged appeal top of mind. The Flint and Tinder Texas Reserve Collection is an outstanding example of top-notch craftsmanship, endlessly cool style points and a nod to Western heritage, done the Huckberry way.

From the richly crafted Waxy Kudo Roper Boots to a line of Flint and Tinder Reserve Denim (crafted from best-in-class selvedge cotton), the new offering is a stellar study in craft, hard work and attention to detail (four different types of selvedge denim certainly nod to that approach).

The great news is, a tough and hard-working pair of selvedge denim pairs up expertly with Western-style boots, along with F&T staples like a handsome roughout trucker jacket or a durable Western denim shirt.

And as Huckberry says of its boot partnership in this collection with famed bootmakers Rios of Mercedes, the family-owned company boasts “rich history that lends itself quite nicely to what the company calls “a one-of-a-kind roper boot.”

And when it comes to the jeans on offer within the Flint and Tinder Texas Reserve Collection, you’ve got your pick from a deep inky black pair of selvedge to classic shade of Khaki and Olive. Each pair of some of the best jeans for men boast a hard-wearing, break-in-ready 13-oz. Japanese fabric that’s also woven on antique shuttle looms — in Texas, of course.

Best selvedge denim for men.

A YKK zipper, hand-numbered labels and sturdy hardware deliver a tough finish and long-lasting wearability, as you’ve come to expect from Hukberry. The bottom hems feature a real selvedge finish, the kind you can show off when cuffing your jeans.

Between the incredibly well-made, frankly beautiful roper boots and a selection of old-school selvedge denim, it looks to me like the Flint and Tinder Texas Reserve Collection hits the mark on the head when it comes to both the old-world and the modern — get your pair of boots (or jeans!) while they’re still in stock.

The Friday Read: The Best American-Made Menswear From Devium, A New Huckberry Jacket & A Winter Weekend Getaway

Devium menswear review.

It can sometimes be tough to find a brand doing things the old way — the hard way, the difficult way, like making some of the best American-made menswear. It’s something I’ve had the time to think about this week as we come to another edition of the Friday Read here at your favorite Brooklyn style blog.

And as with past menswear reviews on this site — including last week’s introduction to Vero Watches — I’m all about brands that go the extra mile when it comes to quality and craftsmanship, like California-based Devium.

The decade-old brand puts its money where its mouth is, so to speak, in matters of rugged workwear, American-made production and a full array of timeless styles (think hard-working trucker jackets, flannel shirts, canvas workwear, durable chinos and much more).

The Devium story — which starts with the company’s founding on Flag Day, of all days, in 2015, is an impressive one, with plain old fashioned hard work and 100 percent American-made construction at its core.

I’m excited to learn more about the brand, and I’d wager you’ll feel the same way as you dive into its flagship lineup, which includes a range of sturdy flannels, tough-as-nails waxed jackets and more. How’s that for a new brand to jumpstart your weekend? T

he company makes the sort of dependable, good-looking, hard-wearing menswear that should prove useful in plentiful style situations, including my next jaunt — my first trip of 2025, in fact, and a suitably winter-focused one.

I’m off with my love Mary to chilly Stroudsburg, Pennsylvania, where a relaxing family weekend — think flannel shirts, whiskey, great food and even better times — awaits. To see how I’m outfitting myself and to find out what I’m sipping on, head over to my Instagram.

And before we head off into the weekend properly, let’s talk briefly about another must-buy style essential, the sort that should come in remarkably handy in terms of warmth, toughness, sturdy construction and long-lasting appeal.

Flint and Tinder waxed jacket.

What style selection could clear that very high bar and live up to the hype at the same time? The new Flint and Tinder Flannel-Lined Hooded Waxed Jacket, of course. Crafted from the same Martexin waxed sailcloth as the positively legendary, best-selling Flint and Tinder Waxed Trucker Jacket, the style adds a weather-ready waxed hood and keeps the same classic detailing, like durable hardware and a striped blanket lining.

Flint and Tinder Hooded Waxed Trucker Jacket review.

It’s a workwear jacket built to last in every sense of the word, and it comes in two must-have colors: Field Tan and a rich shade of Forest. Either is a fitting addition to a highly functional, carefully considered and casually rugged (and useful) winter weekend wardrobe.

Between Devium and Huckberry, if you ask me, I’d say you’ve got plenty of gear to consider in the days ahead — and plenty of gear to break in and make all your own. Happy shopping and cheers to American-made menswear, my friends.

The Tuesday Steal: Amp Up Your Casual Style Rotation with this Flint and Tinder Hat from Huckberry

Flint and Tinder ballcap.

Just as no man is an island, no one’s rotation of the best menswear essentials is ever quite fully complete, or fully finished…. right? At least, that’s the case if you believe in the small details making the difference, and in the need to complement a casually rugged #OOTD the right way.

In the case of today’s standout featured pick — a pick you should just buy if you’re search of an expert way to top off your outfit — the details certainly count. That’s because we’re talking about a Flint and Tinder ballcap, one made the right way, the proper way by the good folks at Huckberry — the sort of ballcap that might put other casual ballcaps in your rotation to shame.

That’s lofty praise, to be sure, but for under $40 on sale at the moment, the Flint and Tinder Waxed Canvas & Corduroy Hat hits on all the marks you’d expect from an accessory bearing the praise-worthy F&T designation. For one, the Flint and Tinder Waxed Canvas & Corduroy Hat is truly a ballcap that can take a beating come fall and winter, and that’s not to be overlooked

Sure, it might not be the hat you’d reach for in the depths of a blizzard, of course (save a Huckberry beanie cap for that). And yet, its waxed canvas crown is nicely complemented by a seasonally friendly corduroy brim for texture, style and toughness.

In fact, the Flint and Tinder Waxed Canvas & Corduroy Hat might break in just as nicely as your favorite Flint and Tinder waxed trucker jacket — if you’ve had one of those covetable trucker jackets in your rotation for years, then you know that Huckberry means business.

Flint and Tinder ballcap review.

It’s as if this cap (assuredly one of the best ballcaps for men) was made to pair up with rugged picks like a denim sherpa jacket or a flannel overshirt and a sturdy pair of blue jeans. Beyond that, the right ballcap shields your face from sun, rain and wind, proving critical in times of work and times of leisure (another round of brewery beers, anyone?).

Details like the leather strapback and brass fastener further deepen the durability of the Flint and Tinder Waxed Canvas & Corduroy Hat, at least in my experience. And while that might be lofty praise to call it one of the best men’s hats on the market, it’s certainly a fine deal at the moment for under $40.

The Friday Read: A New American Watch Brand Worth Knowing & The Best New Gear from Huckberry

VERO watches review.

Welcome back to this, the second Friday Read of 2025. It’s a worthwhile time to take stock of how your year has started and where you want it to go, in matters of New Year’s resolutions — menswear and otherwise — in matters of how you dress and the mindful thought that goes into some of your favorite menswear brands. Now, to be sure, I’m not just talking about tried-and-true, fan favorite brands like Huckberry.

We’ve already talked about the best Huckberry menswear in particular to start 2025, but let’s go beyond just that, shall we? In fact, in future editions of the Friday Read, you can expect the occasional spotlight on an unheralded yet truly excellent brand, like the USA-made timepiece manufacturer we’re about to discuss, Vero Watches.

As of late, my attention has been captured by some similar upstarts, the sort of brands that fall right in line with the rugged, adventurous, tastefully classic yet modern vibe of Huckberry (and Taylor Stitch, and Buck Mason and … well, you get the picture).

Best field watches for men.

And especially in the wristwear arena — as I cover watches frequently for Maxim.com and elsewhere — I’ve been impressed by the revamped takes on the “modern American field watch” coming out of Vero Watches. The brand was actually founded back in 2015, but has started to garner some buzz as of late, and I appreciate their outdoor-ready, rugged and yet crisply designed sensibility as far as watch design is concerned.

Vero men's watches review.

And to hear the company tell it, its timepieces are “inspired by grit, commitment and style,” with a true sense of intention behind each timepiece (like the Workhorse Chrono shown here). In fact, Vero Watches says they build timepieces “that are meant to live on your wrist,” rather than in a collector’s box. An admirable focus, yes?

Many of its watches are built with durable stainless steel, feature hearty water resistance and outdoor-minded features like canvas straps, and of course, production takes place in the good ole U.S. of A — Portland, Oregon, mind you.

Yessir, if you ask me, there’s a lot to love about this brand, including the beefy 44.5mm case build of the Workhorse Chrono (expect more in the weeks ahead on this particular watch, my friends).

Consider this your first intro to Vero Watches, a brand I’ll surely be circling back to here on the blog in good time. As it were, you very well might be able to spot a timepiece from the company sooner rather than later on my Instagram.

Best field watches for men.

For now, I’m going to wind down this Friday Read early — you’ve got some reading and shopping to do as far as your new favorite watch company is concerned, but if I can recommend one final piece, head over to yesterday’s blog post to revamp your weekend activewear and loungewear game from Huckberry. Cheers to a new year, a fresh weekend and some stylish recommendations to power the days, weeks and months ahead.

The Thursday Buy: Start the New Year Off Right With the New Wellen WellKnit Sweats from Huckberry

Best sweatpants for men in 2025.

For as much fun as it can be to look back on a holiday season filled with joy — and Christmas cookies, and whiskey, and craft beer — at some point, a guy’s got to get back to work and the right daily style essentials can help. That process includes the real work of your daily grind, and ideally, even the real work of a wellness routine, however that shakes out for you.

And a must-have in any sort of wellness routine — or a travel wardrobe, or for a weekend coffee run? A pair of the best sweatpants for men, something that the good folks at Wellen and Huckberry seem to have excelled at crafting for the new year (and beyond).

In fact, the entire Wellen WellKnit line takes things to another level in terms of performance, sustainability and even a dash of minimal style. All are valuable to have close at hand as you plot your next road trip, your next morning yoga session, your next park stroll or your next weekend coffee outing (again, I’m something of a coffee fiend, and I trust the best loungewear to get me from point A to point B in style).

If any or all of the above pursuits sound like you, then you’d do well to scope out the entire Wellen WellKnit line, particularly the ultra-soft, ultra-stretchy and performance-minded Wellen WellKnit Joggers.

The use of four-way stretch, proprietary fabric — complete with a tapered fit for streamlined performance — makes these the ideal men’s jogger pants for weekend outings, morning training sessions and just about anything you can dream up (yes, lounging very much included). Plus, hidden features like side hip pockets — complete with inner stash pockets for 2-in-1 functionality — make the Wellen WellKnit Joggers a prime purchase in any one of four neutral, versatile colors.

To ramp up your storage to the next level, a back zip pocket provides even more space for daily carry essentials. From the ultra-soft fabric to the next-level tapered fit and a slew of performance features (including moisture-wicking, anti-odor fabrication), you could easily say the Wellen WellKnit Joggers are the best men’s sweatpants to buy in the new year.