The Thursday Buy: Shop Huckberry’s Annual Pappy Van Winkle Giveaway Right Now For a Chance at $12K (And Rare Bourbon)

Huckberry Pappy Day 2024.

My friends, the time is now upon us once more. Or rather, if this caught you off guard, it’s time to hit the pause button and head over to Huckberry to shop a deal that only comes around once a year: The famed retailer is giving you (yes, you!… and me!) a shot at some serious cash and some ultra-serious bourbon.

Pappy Van Winkle Family Reserve Bourbon.

The maker of your favorite trucker jacket, the perfect pair of jeans and some of the best men’s boots on the market (among many other things, naturally) is bringing back its 11th Annual Pappy Day, a heck of a deal for lovers of rugged fall fashion and some of the best whiskey on the planet.

Here’s the deal: Now through September 26th, spend $75 on any U.S. order of the best menswear and gear from Huckberry, and get entered to win $12K in cash and a bottle of the covetable Pappy Van Winkle Family Reserve 20 Year.

How’s that for a standout deal on your new favorite fall menswear (and your new favorite bourbon)!? If you ask me, not much more needs to be said today, although might I recommend picking up a pair of the best men’s Chelsea boots or the iconic Flint and Tinder Waxed Trucker Jacket?

Here’s wishing you all the best of luck, the best of shopping some new seasonal style favorites, and hopefully, a toast with the best bourbon on the market. We’ll see you all tomorrow, my friends — now, start that shopping spree.

See Now, Buy Now: Shop the Red Wing Heritage Weekender Chukka at Huckberry Just In Time for Fall

Red Wing Heritage Weekender Chukka Boots review.

If durability, classically cool style and rugged appeal are the name of the game — which they very much are — then it’s hard to pass up Red Wing Heritage and its selection of iconic, incredibly well-made leather boots and shoes. And that’s certainly true now as it was decades ago, which brings us to the Red Wing Heritage Weekender Chukka, an utterly classic men’s boot style that’s stood the test of time.

Speaking of time: They’ve landed back in stock at Huckberry just in time for the fall season ahead, and they couldn’t be a more ideal wardrobe addition if you’re all about classic, dependable style. When it comes to the Red Wing Heritage Weekender Chukka, the specs are on point across the board, and quite literally from the ground up, in this case.

Certainly, this isn’t the first time you’ve read about some of the best boots for men, particularly from Red Wing Heritage on the blog, and it won’t be the last. Let’s carry on, shall we?

It starts with tough-as-nails S.B. Foot Tanning Company leather, which is then stitched down for a resoleable design, while a chunky Hill outsole adds toughness and traction.

The combination also includes a Texon® board insole that molds to your foot over time, while the ComfortForce footbed amps up the premium, comfortable nature of some of the best boots for men.

Add in the fact that the Red Wing Heritage Weekender Chukka manage to repel water, stains and perspiration, and you’ve got a reliable pair of boots that perform just as great as they look. Of course, the silhouette of the Red Wing Heritage Weekender Chukka is iconic and as wearable with rugged selvedge denim and a henley as it is with stretch five-pocket pants and a crisp Oxford shirt.

There are few men’s boot styles as beloved, long-lasting and well-made as the Red Wing Heritage Weekender Chukka, which is why it’s certainly worth a reminder that they belong in your early fall wardrobe.

See Now, Buy Now: This Portuguese Flannel Chore Coat from Huckberry Is Perfect for Early Fall

Best men's chore coat for early fall.

If it feels somewhat strange to be talking about the best style essentials for early fall as of yet, well, check that calendar: It’s nearly here, and with Labor Day bearing down on us, it’s high time to start think about a few key fall style upgrades for men. Naturally, I’m recommending you head to Huckberry to start your search, which is where we’ll take a peek behind the curtain today at one of the best chore coats for men.

One of the best jackets for men is our focus today, and not just any old style, either. Huckberry, if you’ve dove into the Web site as of late, knows how to curate, sell and style a slew of classic pieces, including an iconic chore coat from Portuguese Flannel.

The Portuguese Flannel Labura Corduroy Chore Coat perfectly bridges the gap between rugged style and modern good looks, with real-world utility at its center (its core?).

Best corduroy chore coat for men.

The key with the Portuguese Flannel Labura Corduroy Chore Coat starts with its silhouette — it’s modeled after throwback chore coats featuring patch pockets and a useful stand-up collar. And another key when it comes to the handsome, versatile Portuguese Flannel Labura Corduroy Chore Coat?

Its use of soft cotton corduroy fabric, a helpful touch that makes it easier to move around in than a traditional canvas chore coat, for instance. Your new favorite chore coat also boasts a tailored fit that’s still easy to layer, be that over a classic chambray shirt, an easygoing T-shirt or a rugged henley.

The Portuguese Flannel Labura Corduroy Chore Coat also looks great with stretch chinos, with contrasting faded blue denim or even with olive canvas work pants for days at the shop (or a more blissful coffee shop outing, of course).

Particularly with its corozo button front, this stylish and classic chore coat even looks a touch more refined, especially as a suitable blazer replacement. For early fall layering and beyond, I think I’ve found my new go-to layer, and it’s the Portuguese Flannel Labura Corduroy Chore Coat

The Friday Read: Smart Casual Summer Style from Huckberry

When some things work, you know it right away in terms of your wardrobe of menswear essentials. That’s the topic up for debate — or rather, no debate at all — in today’s Friday Read, and that’s thanks to my good friends at Huckberry.

The classics are the classics for a reason, in terms of both effortless style and versatility, and the famed retailer just gets that right in every way possible via the latest and greatest Huckberry Smart Casual offering.

The Huckberry Smart Casual offering has a little something for everyone, especially headed into a packed Brooklyn weekend for yours truly (and beyond, of course). For days at the office and wedding weekends in particular, Huckberry just delivers, and that holds true from season to season and situation to situation.

As the brand says, the Huckberry Smart Casual rotation includes breezy polos, iconic T-shirts, rugged leather jackets and expertly faded denim, to name but a few favorites. These are the kind of pieces you can mix and match with effortless ease, particularly leading from summer into early fall.

For smart casual style, look no further than the Huckberry Smart Casual rotation this weekend — that’s my latest and greatest #menswear tip heading into the weekend, and you can look for more where that came from very soon indeed.

The Sunday Sale: These Stylish Astorflex Loafers are 40 Percent Off Now at Huckberry

Best leather loafers for men.

I don’t know about you, but just when it seems like I’ve sorted out my summer footwear rotation, I find another pair of stylish men’s shoes worth adding to my rotation. In that case, that’d be leather loafers from the good folks at Huckberry — a pair made by family-owned factory Astorflex no less.

Perhaps you know Astorflex from the craft they’ve perfected, making some of the best chukka boots, but consider these sleek Astorflex leather loafers a worthwhile addition to your wardrobe as summer rolls on.

Astorflex leather loafers review.

And yes, in my book, there’s still more than enough time to step into (and properly style) these Astorflex Travel Loafers, which boast handmade construction, a durable rubber heel for added grip, and a low profile you can dress up or dress down.

In my experience, I’ve found these unlined leather loafers wear incredibly easily right out of the box, they pack up nicely in my favorite weekender bag, and they only get better and more supple with age. And yes, as an added bonus, your new favorite pair of leather loafers are now 40 percent off at Huckberry. Go forth with style in mind the rest of summer, my friends.

See Now, Buy Now: Dress for Cool Summer Nights with This Vintage Long-Sleeve Tee from Huckberry

Huckberry men's T-shirts.

In my experience, sometimes, you don’t know how valuable some casual men’s basics can be until you’ve gone without them. For instance: On a cool summer night around a bonfire or during a beach sunset stroll, ever been caught without an extra layer? I’m not talking about a heavyweight flannel shirt or a thick hoodie — I’m talking about something like one of the best long-sleeve tees to throw on atop your favorite pair of lounge shorts, especially one from our friends at Huckberry.

It’s an underrated style essential that’s served me well on many a summer beach vacation, especially as cooler weather beckons through the end of late summer. And today, well, you’re in good hands, since Huckberry’s new Trumbull line of American-made basics delivers one of the best long-sleeve tees for men.

It’s an indisputable workhorse, a well-made tee in its own right and a casually cool menswear move to end the season. Heavyweight cotton construction (garment-washed for softness) gives the Trumbull Vintage Wash Long-Sleeve Tee a lived-in feel, just like the kind of tee you’d unearth from a lakehouse closet on a crisp night.

And yet, this stylish men’s long-sleeve tee sits ready and waiting in your T-shirt drawer or your favorite weekender bag without missing a beat — since, well, you’ve hopefully already added it to your cart in a trio of stylish colors.

Best long-sleeve T-shirt for men.

With its durable made-in-Detroit construction, its relaxed fit (ideal for layering atop a short-sleeve tee with room to move), and its vintage-style look, it’s a perfectly neutral basic you can even layer beneath a trucker jacket alongside blue jeans.

But for transitional style — especially in coastal settings where you need a warmer layer alongside your go-to shorts — I’d say the Trumbull Vintage Wash Long-Sleeve Tee is a surefire bet as far as laidback summer style goes. Try this one on and report back in the comments if you’re a fan. Cheers and thanks for reading!

The Thursday Buy: These Flint and Tinder Stretch Selvedge Jeans are Your New Go-To Pair

Best selvedge jeans for men.

There are plenty of men’s style essentials I simply can’t get enough of in my daily rotation, particularly from Flint and Tinder and the good folks at Huckberry. That list includes a pair of the best men’s jeans, which Huckberry just seems to keep getting better at crafting, and it doesn’t hurt that Flint and Tinder already has the chops as far as crafting rugged style staples is concerned (See: Your favorite waxed trucker jacket, for starters).

Best selvedge jeans for men.

And the Flint and Tinder Stretch Selvedge Jeans are yet another fitting entry into a well-curated lineup of daily style must-haves, with the specs to run with the best of ’em. Available in both Slim and Straight fits — either of which should prove flattering and versatile — your new favorite blue jeans come in a year-round selvedge denim weight that’s been amped up with a hint of stretch.

The Flint and Tinder Stretch Selvedge Jeans also boast classic selvedge detailing, in addition to a durable weave and design that, as Huckberry says, makes you realize that it’s “no wonder denim enthusiasts call it a favorite.” That goes for my personal experience with some of the best selvedge jeans for men, and I also can’t help but appreciate the vintage-inspired wash (among a trio of options in which you can find the Flint and Tinder Stretch Selvedge Jeans).

Details like durable, tough hardware — a Flint and Tinder staple — and a custom suede Flint and Tinder back patch round out these stylish men’s jeans quite nicely, as well. And when paired with your favorite henley and a tough-as-nails waxed trucker jacket, the Flint and Tinder Stretch Selvedge Jeans very nearly take the cake as some of the best jeans for men on the market. Try ’em on for size and see for yourself.

The Sunday Sale: It’s the Last Day to Shop the Huckberry Annual Summer Sale — Stock Up As Soon as Possible

Huckberry Summer Sale 2024.

In the world of menswear essentials, there’s nothing quite like what you might call a “measure twice, cut once” approach. That could mean carefully scouring the market for pieces you love, pieces you need, pieces that can expand your wardrobe of menswear essentials the right way.

And then, when the time comes, carefully moving forward with your purchase — again, measure twice, cut once. That’s perhaps no more true than with the Huckberry Annual Summer Sale — bear with me here, folks. We talked earlier in the week about some of the best menswear deals on the market, with savings on everything from the best sneakers for men to the best summer shorts, sunglasses, everyday carry essentials and more.

And now, well, the time has come to make a move, to get down to the “cutting” part — the time has come to add to your cart, make a purchase or two and get a move on, because it’s the last day to score some savings via the Huckberry Annual Summer Sale. See, doesn’t that make perfect sense?

The savings are excellent at the moment (up to 40 percent off, as we talked about earlier this week) and again, there’s a bit of everything up for grabs, from utility shorts to backpacks to hiking sneakers via the jam-packed Huckberry Sale section. The clock really is ticking, so take careful note of what your wardrobe needs, then act accordingly on the last day of the action-packed Huckberry Annual Summer Sale.

The Tuesday Steal: Take Up to 40 Percent Off at Huckberry’s Annual Summer Sale

Huckberry Summer Sale 2024

The most wonderful time of the year is normally an apt moniker for a much later season, but when the Huckberry Annual Summer Sale rolls around, things change just a bit. It’s as solid a seasonal sale as any on the market, with the lauded retailer giving you up to 40 percent off on, well, a bit of everything from its famed wares.

The Huckberry Annual Summer Sale runs the gamut from menswear to outdoor gear, camping gear, everyday carry essentials, the best men’s boots and sneakers… the list goes on. If you can dream it up in your wish list, you very well might be able to find it via Huckberry.

Flint and Tinder 365 Shorts review.

In taking a quick spin through the standout assortment of the best men’s gear at Huckberry, you’ll find not only classic brand picks like the Flint and Tinder 365 Shorts, but also newer style steals like Walden Eyewear sunglasses, Flint and Tinder chambray shirting and sleek loafers to top it all off.

The combinations are nearly endless, the deals run through Sunday, July 21st (expect another reminder before then), and you’re going to love what lands on your doorstep very soon from the Huckberry Summer Sale 2024 — take it as a guarantee, at least in my experience with one of my favorite online brands.

See Now, Buy Now: The Sperry Authentic Original Boat Shoes Are a Must-Have Summer Essential

There are some men’s style classics that are so prevalent, so widely seen, it can be tough to recognize them for what they are — a must-have for your own wardrobe, in addition to being a much-loved favorite, for instance.

In my experience, that’s what the Sperry Authentic Original Boat Shoes represent, especially in my own wardrobe: A tried-and-true summer essential that’s stood the test of time, one that’s as versatile as can be and as wearable now as it was decades ago. Add in the fact that your new favorite boat shoes are now sold by Huckberry, and you’ve got a certified style winner on your hands.

What makes the Sperry Authentic Original Boat Shoes a prep staple as well as an easygoing style move nearly any day of the week (at least in off-duty situations)? It could be the premium handsewn leather upper and classic moc toe construction, or it could be handsome touches like rawhide laces for a dash of throwback style.

Or perhaps it’s the wearability of the Sperry Authentic Original Boat Shoes — they team as easily with rolled light wash jeans and a camp collar shirt as they do with your favorite polo and chino shorts.

Best boat shoes for men.

Plus, the Sperry Authentic Original Boat Shoes feature an EVA midsole for comfort and rebound, plus a non-marking outsole for the right blend of traction and long-lasting wearability. Rich leather options abound when shopping for these stylish boat shoes at Huckberry, and the two-eyelet lacing system is casually cool while delivering a snug, customizable fit.

Sperry Authentic Original Boat Shoes.

Better still is the fact that the Sperry Authentic Original Boat Shoes retail for a very agreeable $110, giving you the chance to snag more than one pair if you so choose. For the right mix of classic style, great looks and laidback wearability, reach for the Sperry Authentic Original Boat Shoes — they’ll get the job done, and then some.