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.

The Sunday Sale: Save on the Best Everyday Menswear With the Bonobos Winter ‘Sale on Sale’

No matter how well-stocked you might find your daily menswear wardrobe, there’s always time for reflection or for an examination of what you might need — but let’s stay away from overly extravagant purchases and focus on the daily essentials that yes, you do truly need.

A crisp pair of pants for the office, an Oxford shirt you can wear solo or layer up, even a reliable topcoat that you can wear with virtually any outfit in your rotation… and yes, it’s worth considering a brand that can help get you there. My friends, let’s return once again to the ever-versatile, crisply designed and carefully fashioned stylings of Bonobos, the venerable NYC menswear brand approaching its 20th anniversary.

I’ve covered Bonobos plenty in Bonobos reviews over the years on this style blog, and while the brand’s scope has expanded beyond just the best chinos for men, there’s still something to be said for the quality and performance of its retooled lineup (at least, that holds true in my experience).

And there’s never been a more prime opportunity to find precisely what you need for the office, for date night or as you search for what to wear on Valentine’s Day. How so? The Bonobos Winter ‘Sale on Sale’ is here for a limited time, with savings so good, you very well might look at least twice.

With the simply excellent Bonobos Winter ‘Sale on Sale’, you can take up to 50 percent off already on-sale items for a grand total of as much as 70 percent off. A whopper of a deal as we cruise into the next stretch of winter, yes?

The Bonobos Winter ‘Sale on Sale’ delivers the goods when it comes to a slew of easily wearable everyday classics, including the stretchy yet sturdy Bonobos Travel Jeans (a personal favorite), plus crisp everyday shirting, cozy sweaters and more refined selections like the Bonobos Jetsetter British Wool Blazer as shown above.

How’s that for the perfect mix of savings and style? I very well might be biased, but I’m quite simply a fan of darn near everything Bonobos does –an expert blend of accessibility, attention to detail, modern style and classic good looks. And yes, that’s high praise, but it’s yours for the taking via the Bonobos Winter ‘Sale on Sale’. Happy shopping, folks.

The Sunday Sale: Shop and Save on the Best Winter Menswear with this Bespoke Post Apparel Sale

If you ask me, the new year has brought wave after wave of stellar, rugged, stylish and classic menswear — yes, menswear that checks each of those four tricky boxes certainly hasn’t been in short supply, at least if you ask the writer behind this Brooklyn style blog (that’d be yours truly, of course).

And the hits keep coming, especially if you want downright useful menswear you can rock all winter long — starting right now.

You needn’t wait for the end of the season to score savings on cozy, durable and dependable winter menswear — the Bespoke Post Winter Apparel Sale helps see to that, with automatic savings applied at checkout, no discount code needed. How about that?

The Bespoke Post Winter Apparel Sale features some of the company’s greatest hits, including discounts on its in-house brand Line of Trade — think textured crewneck sweaters, dependable wool zip jackets and shirt jackets, quilted bomber jackets and a range of garment-dyed and vintage-style knitwear.

The offering is as packed as can be, but that’s only the tip of the iceberg at this simply outstanding winter menswear sale, my friends.

There’s also a range of utterly classic Line of Trade outerwear, often modeled on heritage military styles and featuring period-accurate detailing and design inspiration. That reliable design holds true for the brand’s deck jackets and shirt jackets, along with its workwear chore coats, each of which are up for grabs at a discount via the Bespoke Post Winter Apparel Sale.

And these are savings simply not to be missed — this sale earns you $50 off orders of more than $175 (a solid discount indeed considering how affordable Bespoke Post menswear and gear can be, all without skimping on quality).

Meanwhile, orders of more than $300 earn you $100 — again, those are savings I can get behind via one of the best online menswear shops for guys.

From rugged shirt jackets to cozy plaid flannel shirting, classic chinos, sherpa trucker jackets and vintage-inspired sweaters, the roster is absolutely packed right now via the Bespoke Post Winter Apparel Sale — load up your shopping cart and watch the savings pile on, my friends.

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.

The Sunday Sale: Start the New Year Off With These On-Sale Mack Weldon ACE Sweatpants

Perhaps it’s the oft-frightful weather outside, or perhaps it’s the cozy nature of this time of year — the laidback, leisurely doldrums between Christmas and New Year’s that we’ve talked about so frequently these days on this Brooklyn style blog — but if I were you, I’d be setting my sights on acquiring the best winter style essentials. I’m not talking about the same-old, same-old sort of picks as far as loungewear is concerned, either.

I’m talking about scouring the market for a brand like Mack Weldon, a company well-known for its focus on performance silhouettes and modern picks for the modern man, including the ultra-cozy and comfortable Mack Weldon ACE Sweatpants.

Best sweatpants for men.

Make no mistake: The brand really can do it all, though. For the more refined moments in your rotation, the Mack Weldon WARMKNIT Cardigan harnesses the perfect fusion between function and form with ultra-soft, warm and yet sturdy fabric, but the brand’s sweatpants (and T-shirts, and henleys!) are perfect examples of how casual style staples can be made the right way — and then some.

With winter’s worst upon us, the best men’s sweatpants are going to prove ever-critical for laidback lounging at home or on the road that you can feel great about — the essential Mack Weldon ACE Sweatpants are also as primed for at-the-gym performance as they are for streamlined comfort on the go, and right now, your new favorite sweatpants are about 40 percent (a perfect pick for the first Sunday Sale entry of 2026, wouldn’t you agree??).

It comes down to the proper fabrication and design, of course, and the Mack Weldon ACE Sweatpants get the details right every step of the way. Micro-brushed French terry fabric delivers maximum softness and comfort, while ribbed ankle cuffs provide a secure fit and classic jogger style.

The Mack Weldon ACE Sweatpants are also adorned with what the brand calls a stealth zip pocket for small everyday carry essentials, while the thick drawcord waistband mimics the brand’s standout boxer briefs and underwear with a no-fold, no-rollover design (plus stretch and comfort, naturally).

Available on sale right now in two crisp color options, the no-nonsense, ultra-comfortable and sleek Mack Weldon ACE Sweatpants are a perfect fit for laidback days at home, intense training sessions and even time spent out on the road in 2026. Find your perfect pair and perfect fit on sale now.

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 Sunday Sale: Save More Than 30 Percent On this Layering-Ready Merino Sweater from American Trench

Best sweaters for men.

There’s no time like the present, as we often say, to upgrade your seasonal style game, and more specifically, your seasonal layering rotation with one of the best sweaters for men. I’d wager it’s also an apt time to go a step further and reach for one of the best American-made sweaters — not an easy thing to do in this day and age and in this economy, but a goal made all the easier by American Trench, long one of my favorite brands for its steadfast commitment to honest-to-goodness American-made production and stylish designs aplenty.

The brand has a serious knack for putting plenty of care into every stitch, be it the company’s famed American-made American Blazer or its thick-knit, colorful and exceptionally high-quality USA-made socks. which happen to be a personal favorite of my own menswear rotation.

And the American Trench Merino Nautical Sweater carries on that tradition and commitment to quality in fine fashion, and it does so at more than 30 percent off right now — talk about a heck of a deal for a hard-to-find American-made sweater from a top-notch producer.

There’s a sense of care and craftsmanship to the American Trench Merino Nautical Sweater, which borrows from utterly classic Breton stripe sweaters famously worn by the French Navy.

With its rubbed cuffs and hem, it should prove a snug, comfortable layer ideal for wearing atop a white Oxford shirt to the office, out and about on a date atop a blue denim shirt or paired up in easygoing fashion over a long-sleeve cotton tee for laidback weekend style.

When a sweater like the American Trench Merino Nautical Sweater comes along, complete with remarkable merino fabrication for temperature regulation and anti-odor properties, it’s certainly worth considering — and with winter’s worst weather rolling into town, you’re going to need a full assortment of the best sweaters for men. The good folks at American Trench can assuredly help.

The Sunday Sale: Filson’s Black Friday and Cyber Monday Sale Offers Up Rare Discounts on the Best Outdoor Gear for Men

Filson menswear 2025 review.

There are times when you’re hard-pressed to find some rare, exclusive savings on one of the best heritage menswear brands on the market. As it turns out, ongoing Black Friday and Cyber Monday deals aren’t quite one of those times — it seems plenty of the best online menswear brands, even companies that don’t normally offer up all that many discounts — are getting in on the fun in a big way.

At least, it’s fun if you love the best rugged gear for men, which if you happen to be reading this blog, well, I assume you do! And that brings us to the famed Pacific Northwest gear purveyors at Filson, long one of my favorite brands and a reliable stalwart as far as the best men’s adventure supplies and apparel is concerned.

Of course, it was with great interest that I caught wind of a hidden gem, so to speak, in a crowded market for top Black Friday sales and deals: The Filson Black Friday Sale delivers 25% off more than 100 products from the famed style and apparel brand, each as built to go far afield as the next.

It’s truly a sight for sore eyes (or at the very least, a sight for your wallet), as a host of tried-and-true Filson favorites are delivering nothing but the utmost in dependable performance and heritage-worthy great looks.

That’s certainly not hyperbole if you ask me: Peruse the wares on sale for a very limited time at the Filson Black Friday Sale,and be amazed at what you’ll find. The iconic Filson Tin Cloth Lined Short Cruiser Jacket is a brand flagship that gets the proverbial red-pen discount, while the Filson Rugged Twill Duffle Bag lives up to its hard-wearing name.

On the apparel front, the Filson Alaskan Guide Shirt is a legend in the category, with rich warmth and plenty of craft in every stitch. That Filson mantra (“unfailing goods since 1897,” lest we forget), definitely holds true even as gear goes on sale (and a heck of a sale, at that!) through discounts only available for a few more days via the Filson Black Friday Sale.

When a heritage sale comes a-knockin’ featuring a brand that’s hard to find at a discount, you best pay attention — and keep your credit card at the ready, of course. Cheers to holiday deals, my friends.

The Sunday Sale: This Garment-Dyed Blazer from Wills and Huckberry is the Most Versatile Jacket You Can Buy (At a Discount)

I often scour the market for the best men’s clothing deals, as you well know if you read this Brooklyn style blog on the regular. Of course, I frequently check out the digital wares on the (digital) shelves at Huckberry, which is what brings us to today’s Sunday Sale in the midst of a very fine NFL fall Sunday indeed.

And in the midst of an utterly jam-packed holiday season, it’s reassuring to know you can still score a deal on a truly versatile piece of men’s tailoring, like the Wills Garment-Dyed Blazer shown above.

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It’s not the first time we’ve talked about Wills, the ultra-premium in-house brand from everyone’s favorite Americana retailers Huckberry, as the micro-brand is perhaps best known for remarkably soft cashmere sweaters, neatly tailored trousers and easygoing yet luxe staples like the Wills Garment-Dyed Blazer.

Huckberry calls this handsome navy blazer, complete with classic patch pockets, “your secret to easy-wearing warm-weather style,” perhaps a sign pointing towards its on-sale price tag right now — and yet, this is one time shopping out of season, yet at a discount, makes perfect sense.

You see, with a crisply cut navy blazer like this, particularly in a lightweight design, you can layer it up with ease over everything from an elegant button-front cardigan to a fisherman sweater. Thanks to its blend of cotton and elastane, this blazer should prove adept at business casual style situations as well as business casual travel.

After all, the soft-shouldered design and patch pockets make for easy wearability on the go, from point A to point B — and Wills clothing at Huckberry, like the Wills Garment-Dyed Blazer, is also designed to resist wrinkles and odor, not unlike the Proof in-house brand at Huckberry.

With a crisply cut and highly stylish, easily wearable blazer like the Wills Garment-Dyed Blazer, go-anywhere good looks become second nature, be it pairing with an Oxford shirt and rust chinos this holiday season, or else keeping handy to wear with dark blue jeans and a chambray shirt at the office or on a weekend date night.

Throw in the chance to save a few bucks with your purchase, and it’s a no-brainer to scoop up the Wills Garment-Dyed Blazer, at least in my experience.

The Sunday Sale: These Affordable Wellen Joggers from Huckberry Are Your New Weekend Go-To

It’s on a rainy Brooklyn Sunday that I come to you with the latest and greatest deal for your fall and winter wardrobe: A pair of go-anywhere, do-anything joggers that manage to get the job done in matters of style, utility and comfort aplenty.

And while I’m not as much of a gym rat as in my high school and college days, you could certainly find ways to wear the on-sale Wellen Wellknit Joggers for fitness pursuits aplenty as well as laidback weekend lounging — and at this current sale price, you’d be hard-pressed to let them pass you by, especially with Black Friday and Cyber Monday on the horizon.

Billed by Huckberry as “Wellen’s new radically soft performance sweats,” the Wellen Wellknit Joggers are marked down about 20 percent right now, just in time for cozy fall and winter weekends and perhaps even the odd Thanksgiving football game.

The brand’s proprietary four-way stretch fabric is quick-drying and anti-microbial, while the tapered fit is warm-up approved and plenty comfortable for, again laidback lounging (are you sensing a theme here?).

And since the Wellen Wellknit Joggers are part of the always-excellent Huckberry Sale section, it’s worth perusing the famed retailer’s other selections of durable, dependable gear — from whiskey decanters to leather-bound flasks to rugged flannel shirts and warmly knit beanie caps.

And like much of the rest of Huckberry’s gear picks, these stylish, sleek joggers are packed with plenty of bells and whistles — note the inclusion of five pockets, including two side pockets with inner stash pockets and a back zip pocket, all the better to haul your everyday carry essentials.

A drawcord waistband provides a secure fit on the go, while colors like Black, Navy and Natural Heather provide maximum versatility in and out of the gym — plus, throw in on a deal on the ever-useful Wellen Wellknit Joggers, and you very well might want to secure more than one pair. ‘Tis the season for cozy, effortless style and performance, and these joggers from our friends at Huckberry lead the way.