The Thursday Buy: The Newest Huckberry All-Weather Duckboots Are the Best Men’s Winter Boots to Buy Now

Best men's winter boots

If recent weather around the country is any indication, you’re going to need a pair of the best men’s winter boots close at hand, and quickly. We’ve only just now Thanksgiving (thanks for reading on this day, my friends!), but it’s perhaps more critical than ever that you lace up a pair of the best boots for men. That goes doubly so for a pair of the best new winter boots from Huckberry. Or rather, well, these boots aren’t exactly brand-new, but they’re a fan favorite design you’d do well to add to your winter wardrobe.

A new year calls for new adventures...check the national parks off your list as you go!

I’m talking, naturally, about the All-Weather Duckboots, once again restocked alongside a full rotation of the best boots for men, just in time for inclement weather. We’ve talked about Huckberry duckboots in the past on the blog, but it’s always worth a reminder — particularly when the pair in question comes in a cool new Tan and Brown color scheme. Think of them like just a small part of the best Black Friday 2022 style deals, but a critical one all the same.

Best winter boots for men.

The well-made, extremely cool All-Weather Duckboots hit all the right design notes, from the hybrid sneaker-meets-boot build to the tough rubberized rand that protects your feet from slushy inclement weather all day long (and yes, in all types of weather). The All-Weather Duckboots also use waterproof nubuck and full-grain leather for the perfect blend of style and utility, while the Vibram outsole is super-grippy and dependable.

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Of course, it doesn’t hurt that the All-Weather Duckboots are pretty stylish as far as the best winter boots for men are concerned, what with that rugged Tan and Brown color scheme up for grabs. Plus, the All-Weather Duckboots sit atop an EVA midsole for springy comfort on slick, rocky terrain.

If you’re searching for a pair of the best adventure boots, or just a set of the best men’s winter boots for your commute and adventures in the field, don’t pass up the All-Weather Duckboots. Thanks for reading and thanks for trusting The Style Guide with your wardrobe selections — Happy Thanksgiving!

The Thursday Buy: Lace Up Some of the Most Rugged Men’s Boots from FRYE This Winter

Best winter boots for men.

If you’ve kept up with this blog, and with your search for the best winter boots for men, perhaps you’ve happened upon FRYE, the rustic, rugged, all-American company with a penchant for making durable, finely crafted men’s boots. And yet, you might have been waiting for the right moment to add your new favorite pair of boots to your wardrobe. Well, as we cross through mid-November, the right time to shop for the best boots for men is, well, right now.

And that brings me to the cool, throwback-inspired, tough-as-can-be FRYE Prison Boots, some of the most durable men’s boots you can shop right now. If you’ve already shopped FRYE men’s boots in your quest for the best Chelsea boots, consider the FRYE Prison Boots like the more rugged alternative for everyday wear in inclement conditions.

Ideally, these stylish lace-up boots are made to be worn more casually (so, with pieces like the best men’s trucker jacket and your favorite blue jeans), so they certainly check an important box in your winter wardrobe — but that’s not all, my friends.

Most rugged winter boots for men.

The FRYE Prison Boots are just a classic-yet-modern pair of boots made the right way, boasting a Goodyear welt design that means they can be re-soled after years of wear. And given that the FRYE Prison Boots are made in the U.S.A from premium materials (including a sturdy rubber sole), well, you’ll certainly want to wear them as often as possible. The small touches on these stylish boots for men are also done the right way, including the tough waxed fabric laces and eye-catching antique brass hardware.

For good measure, the FRYE Prison Boots boast a shaft height that hits well above the ankle for maximum winter coverage. While the overall design is similar to hard-wearing leather work boots, the FRYE Prison Boots are versatile boots you can style with everything from dressy wool trousers to tailored stretch chinos or even slim black denim for a nice touch of stylistic contrast.

Sizes are going quickly despite the fact that these boots retail for more than $400, a mark of their quality. When it comes time to lace up the best men’s boots, turn to these timeless FRYE men’s boots.

The Friday Read: The Weekend’s Best Shopping Deals, Winter Style & New HIRSCH Whiskey

If you ask me, it seems the menswear calendar has been moving at an ever-faster clip as of late, be it a seemingly earlier-than-usual start to holiday shopping deals or a quicker-than-normal jump to the best Black Friday deals — right after Halloween, in fact. You might recognize that lineup above, filled with some of the best men’s boots, and it’s worth keeping just about every sort of deal in mind heading into Black Friday (even though, for the record, Black Friday doesn’t hit until next week!).

So, take this as a recommendation to start your weekend: My friends at Huckberry are offering some of the best early menswear deals on more gear than you can shake a stick at, so shop accordingly while you plan for the calm before the storm. With that in mind, I’m offering a few more quick pre-Black Friday shopping picks below. And then, well, I’m off to enjoy some rest and relaxation in the Caribbean sun.

If you follow me on Instagram, you know I’ve been on a family vacation to Turks and Caicos since earlier this month, and I’ve got a trip to Florida to follow shortly thereafter. Of course, that won’t stop me from buying the best menswear for fall and winter right now, and it shouldn’t stop you either, my friends. Here’s to holiday shopping early and often, folks.

Best leather boots for men
  • If you keep up with the blog on the regular, I’m willing to bet you’re no stranger to the first entry on my list of recommended weekend shopping picks. Yes indeed, it’s high time you laced up a pair of the best men’s boots from the fine folks at Austin-based HELM Boots, and there’s no time quite like the present to find the rugged pair of leather boots that’s right for you (as I mentioned at the start of this post, after all). Start your search with my thoughts on the HELM Zind Boots, some of the best boots for guys to lace up now.
  • Before you can shop online for the best menswear deals, a bit of refreshment is in order, yes? That’s where my latest whiskey feature comes into play. Over at Maxim, I wrote about (and tasted!) one of the best new whiskies on the market, the new HIRSCH Whiskey Cask Strength Cognac Finish — in fact, I visited the 2022 Kentucky Derby and tried this very bourbon that same weekend back in May. Think of it like a luxe bar cart upgrade to enjoy and savor this winter.
  • Speaking of stylish early holiday deals, here’s another choice pick. Now, not to worry — I’ll have a full guide to the best deals for Black Friday early next week. In the meantime though, head over to the Huckberry Gift Guide and shop the best under-$75 gifts for everyone on your list, be it the rugged man, the whiskey enthusiast or the seasoned style vet.


That trio of style picks brings today’s Friday Read to a close. Whether you’ve got your eye on the best under-$75 gifts or perhaps one of the best new whiskies or even a rugged pair of leather boots, I’m willing to bet your seasonal shopping is off to a good start (I hope!) if you follow a few of the tips above. Stay tuned for tomorrow’s Saturday Style Pick. In the meantime, cheers and thanks for reading! 

Style Pick of the Week: The HELM Boots Zind Boots Are Some of the Coolest Men’s Boots to Lace Up Now

Best fall boots for men.

My friends, if you read the blog on the regular, then I’d wager you know that there’s nothing quite like lacing up a pair of the best men’s boots for fall, right? Think of it like one of the simple pleasures of building a wardrobe from the ground up with the best boots for men and so much more — but of course, in the chilly climes of fall, the right pair of stylish men’s boots is everything. Luckily, that’s where the remarkably stylish, very fast-selling and remarkably well-made HELM Zind Boots enter the equation.

Best men's boots for fall.

Perhaps you recognize the Austin-based brand for its penchant for crafting the best chukka boots for men, not to mention classic leather sneakers aplenty, and HELM Boots is certainly an all-season brand worthy of your hard-earned time and cash. The HELM Zind Boots are particularly special in terms of how they’re built (note the resoleable Blake stitch construction), not to mention the sleek, surprisingly dressy Krumenauer Brush-Off Leather in Burgundy.

That touch makes the HELM Zind Boots readily wearable with everything from tailored chinos to your favorite pair of blue jeans, to name but a few key style picks. You can even top that combination off with one of the best men’s winter sweaters, too. Seriously, these handsome leather boots can do just about anything.


With a pair of rugged-yet-refined men’s boots like the HELM Zind Boots — note the dashing Burgundy color — the world is your oyster, as it goes, in terms of how you style them. In fact, I’d go so far as to say you could wear the HELM Zind Boots with your best fall and winter suit, too. Antique brass eyelets add a touch of throwback appeal, while the entire profile on the HELM Zind Boots is versatile and incredibly, well, cool. The next time you need to lace up a pair of the best boots for men, the HELM Zind Boots are your best bet.

The Thursday Buy: The Astorflex Bomaflex Boots are The Best New Boots to Shop Now

If you ask me, it’s high time you laced up a pair of the best men’s boots for fall, seeing as cold, crisp weather is bearing down upon much of the country in full force. Of course, if you read this blog on the regular, you know precisely where to shop for your new favorite pair of boots: That’d be Huckberry, a personal favorite of mine and a company known for outfitting stylish guys everywhere for adventures aplenty.

That goes for building looks from the ground up with the best leather boots for men, as with the Astorflex Bomaflex Boots — and it also holds true for other Huckberry Bestsellers like one of the best waxed trucker jackets (but I’d wager you knew that already, right?). But back to business and back to your new favorite pair of boots, yes?

Now, what precisely makes the Astorflex Bomaflex Boots so essential to your casually rugged fall and winter wardrobe? It could be the fact that the Astorflex Bomaflex Boots are crafted by the same family-owned factory that makes, for example, your go-to pair of chukka boots, for starters. Or maybe it’s the fact that these reliable boots are made from thick-yet-soft cowhide leather that’s been naturally soaked and dried, all the better to help these dependable boots mold to your feet over time.

Best moc-toe leather boots for men.

The Astorflex Bomaflex Boots only get better from there when you consider the full set of specs, be it calfskin-lined memory foam insoles for extreme comfort, or the lightweight EVA soles for springy cushioning. As luck would have it, the Astorflex Bomaflex Boots blend performance, style and classic looks in one reasonably priced pair of boots (they’ll run you under $350 at Huckberry). The moc toe construction is also durable and timeless, and the fact that the Astorflex Bomaflex Boots also feature boat shoe lacing and detailing is another nice touch.

It’s also worth calling out the wedge sole on the Astorflex Bomaflex Boots, which turns them in to casual boots to wear with blue jeans and a henley, or else with chinos and one of the best shirt jackets on a casual day at the office. They’re also available in goes-with-anything colors like Black or Brown leather, complete with eye-catching rawhide laces. When the occasion calls for modern, rugged style and yet all-day reliability, be sure you’re lacing up the Astorflex Bomaflex Boots ASAP.

The Sunday Sale: Shop and Save Right Now on the Best Men’s Boots from TAFT’s Last Chance Section

Best fall boots for men.

Alright, my friends. Welcome back to another Sunday Sale, where we’re diving into some of the best menswear deals on the market, including the chance to shop and save on the best boots for men from a retailer that knows a thing or two about the category. That retailer would be the impressive E-commerce bootmaker TAFT, a personal favorite of mine when it comes to crafting the best men’s dress boots and plenty (plenty!) more.

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Now, perhaps you’ve had the opportunity to take a look at what I’m recommending today: That’d be a deep dive into the TAFT Last Chance section, which offers deep discounts — in some cases up to 40 percent off — a fast-selling array of the best men’s boots and dress shoes. TAFT specializes in rich, textured leather and sleek silhouettes that lean dressy, but can very easily be paired up with your favorite pair of blue jeans and a rugged henley, for instance.

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The selection within the impressive (and again, fast-selling) TAFT Last Chance section runs the gamut from luxurious hiker boots to some offerings of the fan-favorite TAFT Jack Boots, and that’s just the tip of the menswear iceberg. Remember, you can shop and save on an array of the best boots for men, going as high as 60 percent off. In the depths of fall, that’s a deal worth shopping ASAP.

The Tuesday Steal: Take Almost 20 Percent Off These Rugged Fall Boots from HELM Boots

If you’ve been falling a bit behind on shopping for some of the best men’s boots for fall — to name but one style essential you should shop now — then there’s no time like the present to catch up. In fact, I’ve got even better news for you: You can get a great pair of rugged leather boots for fall on sale right now at Austin-based HELM Boots. Keep in mind that this deal is so stellar (under $250 on sale) that sizing is moving quickly.

Mack Weldon

That being said, it’s not hard to see why: The craftsmanship-focused brand is a favorite of mine, from the best chukka boots to the coolest men’s sneakers, and the HELM Jakob Boots hit similar notes in just the right way.

Best men's boots

For starters, they’re nearly 20 percent off, a nice steal for a pair of well-made men’s leather boots that could quickly become a fall style favorite. They’re inspired by traditional work boots, but the HELM Jakob Boots go a step further with a taller profile, handsome full-grain Krumenauer leather and a super-soft rubber cushioned sole.

Mack Weldon

The Krumenauer leather will get better the more you wear the HELM Jakob Boots, and the fact that you can rock these stylish men’s leather boots with everything from tailored chinos and an Oxford shirt to your favorite henley and blue jeans is a major bonus. The next time you need to lace up the best men’s boots for fall, make sure the HELM Jakob Boots are in your closet — and for a discount, at that.

See Now, Buy Now: The TAFT Mack Boots are Some of the Best Dress Boots to Shop Today

Best men's dress boots for fall

‘Tis the season to… shop some of the best men’s dress boots, if you ask me, and if you’ve been reading your favorite style blog, perhaps you agree. Where to start your search for boots that strike the right happy medium between rugged and refined, between durable, dependable and yet sleek? That answer — at least in my book — is quite easy.

Satchel and Page

Head over to TAFT, makers of a wide range of the best men’s boots (and dress shoes), with enough designs to suit every style. Today though, we’re talking specifically about the TAFT Mack Boots, a versatile and handsome pair of the best boots for men to carry you through this season. I’m also a fan of the more rugged captoe TAFT Rome Boots, and both pairs are worthy of your consideration right now.

Most stylish fall boots for men.

It’s your best bet right now to pick up the TAFT Mack Boots in a brand-new, fall-ready shade of Brown. It’s a deep, rich color that works with fall tones ranging from olive to burgundy to tobacco tan and of course, navy blue as found in the best jeans for men. As luck would have it though, the TAFT Mack Boots have plenty of the right design specs to make them worth your while, too.

Part tailored jacket, part sweater, all versatility.

To wit: The TAFT Mack Boots feature handmade, Blake stitch construction, which makes ’em resoleable after years of wear. They’re also handcrafted in Spain, always a hot spot for the best shoes for men. The brown Spanish Suede upper on the TAFT Mack Boots adds some nice, fall-ready texture and style.

Satchel and Page

What’s more, the sleek wingtip profile should sit nicely underneath everything from an aforementioned pair of the best jeans for men to a fall-friendly wool suit. Between the refined style, the standout construction and their all-around great looks, the TAFT Mack Boots are absolutely worth the price ($295). Style them accordingly today, my friends.

See Now, Buy Now: Prep for Early Fall with Huckberry’s All-Weather Duckboots

Is it ever too early to prep for fall, especially with prepping for fall involves shopping Huckberry bestsellers aplenty? I should certainly think not, and that early fall preparation becomes all the more crucial (and useful) if you happen to be shopping for the best men’s boots for fall (and beyond). You never know when fall weather might strike, or when you might need a new pair of work boots, or rain boots — or better still, work boots and rain boots rolled into one. That leads us to today’s Monday edition of the See Now, Buy Now series, and the Huckberry All-Weather Duckboots. Again, they’re a bestseller at Huckberry for good reason — or rather, plenty of reasons. They’ve been a fan favorite seemingly since they debuted, and they’re back this season in full force. This is very good news for lovers of the best boots for men (guilty as charged there).

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Prep for fall the right way

They’re billed as a waterproof hybrid pair of boots, and not only waterproof – 100 percent waterproof. It’s the kind of attention to detail and an attitude committed to going the extra mile for which Huckberry is known. The Huckberry All-Weather Duckboots are made to be worn around the city through inclement weather on morning commutes, but they also come in quite handy when you hit the trail or dash out of town on fall weekend camping trips. And naturally, if you want a rugged, go-anywhere pair of boots for casual days in the park or at the brewery, the Huckberry All-Weather Duckboots are going to come in mighty handy. It only gets better from there.

SHOP: The Huckberry All-Weather Duckboots

The unbelievably rugged Huckberry All-Weather Duckboots blend the best of both worlds when it comes to form and function. Style-wise, you can select from a sleek all-black pair or handsome brown leather without losing any looks at all. The shock-absorbing midsole should prove remarkably comfortable for long days on your feet, and they’re also built with a breathable membrane to keep your feet from overheating. What does all of this functionality mean for you? It means that these are your new favorite boots for fall, easily. The full-grain leather upper meets the rubberized leather rand design in the front without missing a beat (or allowing water to penetrate the boots, for that matter). It’s all finished off nicely with a super-durable and grippy, high-traction Vibram outsole for maximum reliability on slippery surfaces.

Shop the Huckberry Duckboots now

They’re the best men’s boots for fall

As if all of that wasn’t enough, speed hook lacing gives them a snug fit akin to hiking boots, and yet, the Huckberry All-Weather Duckboots look just as stylish with jeans as they do work pants. Add in, say, a rugged Huckberry henley and a flannel shirt, or else the famed Flint and Tinder Waxed Trucker Jacket (or all three layers), and you’ve got an essential fall #OOTD all sorted out. Plus, they retail for under $200, and you can’t beat that sort of deal on the coolest, most rugged boots for the season ahead.

SHOP: The Huckberry All-Weather Duckboots