See Now, Buy Now: These Beckett Simonon Brogue Boots are the Best Pair of Men’s Boots to Shop Now

Best wingtip boots for men.

It seems hardly a day goes by here on The Style Guide where we’re not talking about the best winter style essentials, including some of the best boots for men — right? Yes indeed, right you are, but that’s not a bad thing in my book. In fact, if you ask me, every style rotation needs plentiful pairs of the best men’s boots, especially from a worthwhile and well-made (extremely well-made!) brand like Beckett Simonon.

The direct-to-consumer men’s footwear brand has been a favorite of mine for years (check out this 2017 Beckett Simonon review), and that shows no signs of slowing down — I’d wager you’ll feel the same way after you learn about what makes the Beckett Simonon Nolan Brogue Boots some of the best men’s leather boots.

Yes, the Beckett Simonon Nolan Brogue Boots are certainly sleek and impressive in matters of style points if you want a pair of the best wingtip boots (the kind you can wear stylishly with everything from tailored men’s chinos to the best blue jeans). But it’s the specs and the standout pricing — try under $240 for some of the best leather boots for men — that really make the Beckett Simonon Nolan Brogue Boots so covetable.

These handsome brogue boots hit on all the right notes when it comes to quality construction and design, including refined full-grain leather and precise brogue detailing. The Blake stitching is resoleable and should prove plenty durable, while a sturdy rubber outsole gives the Beckett Simonon Nolan Brogue Boots some traction on slippery city streets (particularly when styled with one of the best men’s peacoats and wool trousers for holiday parties aplenty).

For the price, you might not find a more stylish, versatile, effortlessly cool pair of boots than the Beckett Simonon Nolan Brogue Boots, and that makes them a worthy holiday and winter style move right now.

Style Pick of the Week: Season Three Ultralight Hiking Boots – The Most Comfortable Boots for Fall and Winter

Most comfortable boots for men this fall.

Folks, step right up and step into the most comfortable boots for fall and winter in today’s prime Style Pick of the Week. It’s a late November weekend, after all, and if you still need to upgrade your fall and winter footwear rotation with a selection of the best men’s boots, you could do worse than picking up a pair of the Season Three Ultralight Hiking Boots.

The NYC-based upstart footwear brand focuses on keeping things subtly stylish, retro-minded and supremely comfortable with its selection of the best hiking boots for men (and women), and they’re a personal favorite of your Brooklyn style writer. And in any style situation this fall and winter, comfort and style are the name of the game — Season Three boots deliver both in spades.

Most affordable hiking boots for men.

The even better news is, these stylish men’s boots are now 40 percent off ($237 vs. $395 full-price). In fact, some pairs of the Season Three Ultralight Hiking Boots are as much as 60 percent off. 60 percent off! So, et’s keep this rolling, shall we?

The best boots for fall and winter, stylish as they might be, are no good if they’re not easy to wear, and luckily for all parties involved, the Season Three Ultralight Hiking Boots deliver on that promise. These sleek yet functional boots are made in a family-owned Northern Italy factory, a haven for the best footwear on the planet. The springy comfort of Ortholite insoles combines with durable Vibram outsoles for a unique blend of traction and exceptional wearability with the Season Three Ultralight Hiking Boots, too. That’s not the only these stylish winter boots have going for ’em.

Best winter boots for men.

Crucially, the Season Three Ultralight Hiking Boots come in a range of cool, eye-catching colors, the kind that call to mind retro hiking boots (especially with contrasting laces in the stylish pair of hiking boots as shown above). Better still is the fact that the Season Three Ultralight Hiking Boots check all the right boxes in other key areas of winter style, too: Just dive into the waterproof nubuck leather found on the Season Three Ultralight Hiking Boots as a starting point.

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For good measure, these stylish men’s winter boots also retain other timeless hiking boot touches, like D-ring lacing and metal hardware. And yet, it all sits atop a chunky, super-comfortable Vibram outsole for plenty of grip on slick city streets and slippery terrain. Yes indeed, the Season Three Ultralight Hiking Boots can do just about anything you ask of them in matters of casual style:

The profile on the Season Three Ultralight Hiking Boots is sleek enough to wear with tailored chinos and your favorite peacoat for polished weekend outings. And once again, here’s the kicker: Right now, the Season Three Ultralight Hiking Boots are on sale for 40 percent off. So, you can get your new favorite pair of winter boots for 40 percent off for a limited time — what are you waiting for, right?

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.

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.

Faherty

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.

Style Pick of the Week: Filson x Danner Trail 2650 Hiker Boots – The Best Fall Hiking Boots for Men

Best hiking boots for men

Sometimes, it takes the perfect menswear partnership to make you think differently about a certain category. Take the best men’s hiking boots, for instance. Hiking boots are certainly functional, but they’re not often all that sleek, stylish or rugged, and not often all three of those things at once — until the advent of the Filson x Danner Trail 2650 Hiking Boots, that is. Think of them like your new favorite pair of hiking boots, and an ideal partnership between Portland-based Danner and legendary Pacific Northwest heritage retailer Filson. Does it get much better than that? Certainly not in my book.

After all, the good folks at Filson definitely know how to outfit guys with the best rugged gear for men, from warm wool jackets to dependable denim and of course, A-plus footwear (not limited to just the Filson x Danner Trail 2650 Hiking Boots, of course). The two brands have, of course, teamed up on the best early fall boots, and this partnership returns just in time for you to get off-trail — or at least get to a cabin getaway — for brisk seasonal adventures. Let’s look more at what makes ’em tick, shall we?

Best fall hiking boots for men.

The Filson x Danner Trail 2650 Hiking Boots are reliable in all the right ways from the ground up, starting with the flexible, lightweight-yet-grippy Vibram outsole for springy comfort on muddy, slick trails. Plus, the Filson x Danner Trail 2650 Hiking Boots are fully waterproof and inspired by the spirit of the great outdoors connecting the two brands — think of them like the perfect blend of throwback Filson style and modern Danner footwear performance. The end result? Easily some of the best hiking boots for men.

Leather and textile GORE-TEX uppers are blended with mesh for breathability while still keeping that crucial waterproof performance intact. They’re the ideal hybrid design to meet the demands of the trail and the town (the Filson x Danner Trail 2650 Hiking Boots are certainly more like sneaker boots than traditional hikers, for starters).

You can wear these stylish, reliable hikers with Filson’s Tin Cloth Pants or with stretch jeans, and of course, the Filson x Danner Trail 2650 Hiking Boots wear nicely with Filson flannel shirting or your favorite henley. The right mix of performance and style is yours for under $220 with this exceptional pair of collaborative boots.

Style Pick of the Week: Wolverine 1000 Mile Roughout Boots – Coolest Fall Boots for Men

When the calendar rolls through fall, that means one thing — if you ask me, at least, that means it’s time to lace up a pair of the most rugged boots for men. And for this Michigan native, that means you need to turn to Wolverine, a longtime favorite and a legendary boot brand. They now do everything from craft the coolest men’s sneakers to, well, the best men’s boots.

Faherty

There are plenty of different editions of the Wolverine 1000 Mile Boots, including the Wolverine 1000 Mile Moc Toe Boots, but right now, the Wolverine 1000 Mile Roughout Boots are the pair to get in your closet and on your feet ASAP. Crucially, the Wolverine 1000 Mile Roughout Boots are based on the brand’s archival 1914 silhouette, with the modern-day, dependable specs to match (keep scrolling).

Best fall boots for men.

As if that wasn’t classic enough, the Wolverine 1000 Mile Roughout Boots feature the brand’s carefully crafted outsole with both Vibram technology and a leather heel. Speaking of leather: The impossibly cool Wolverine 1000 Mile Roughout Boots use rich, textured roughout leather that’s been waxed to bolster its character and good looks.

If you want a pair of stylish men’s boots designed to get better with age, the Wolverine 1000 Mile Roughout Boots should be your next seasonal go-to.

HELM Boots

Better still is the fact that these boots are handmade in the U.S.A, yet the price is much more than agreeable — the Wolverine 1000 Mile Roughout Boots will run you $385, a downright steal when you consider the fact that you can wear them day in and day out in casually rugged style situations from fall to winter.

For starters, pair them with your favorite flannel shirt and the best men’s blue jeans, then keep your season rolling the right way. When the calendar hits October, yessir, go with the Wolverine 1000 Mile Roughout Boots.

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 Thursday Buy: These Danner x Huckberry Boots are the Best Men’s Boots to Buy This Fall

We’ve hit the point in the fall season where you’ve hopefully got plenty of fall style essentials on lock, be it one of the best workshirts, your new favorite henley or of course, a pair of the most rugged men’s boots. That’s where today’s essential Thursday Buy comes into play, and I think you’re going to like what you see. The Danner x Huckberry Waxed Canvas Danner Light Boots are impossibly rugged, well-designed, seriously cool and expertly crafted — and then some. To say they’re everything you should look for in a pair of the best boots for men doesn’t quite do it justice, either. Let’s keep diving in, shall we?

Taft Boots

Of course, the Danner x Huckberry Waxed Canvas Danner Light Boots blend the best of both worlds when it comes to Huckberry’s focus on rugged gear and Danner’s focus on top-notch craftsmanship. The good folks at both companies just understand the spirit of adventure and style — plus functionality.

It all comes together in the Danner x Huckberry Waxed Canvas Danner Light Boots, which blend handsome full-grain leather with upper side inserts made using waxed canvas from Flint and Tinder’s Waxed Trucker Jacket.

It certainly gets even better from there when it comes to the Danner x Huckberry Waxed Canvas Danner Light Boots. This exclusive collaboration (limited to just 600 pairs) turns the already-impressive Danner Light into a thing of rugged beauty, complete with comfort (the Vibram® Christy outsole) and dependability. The Texas Tan leather is stylish and versatile in its own right, while the Danner x Huckberry Waxed Canvas Danner Light Boots offer a snug fit in extreme conditions thanks to speed lacing on the upper.

If you want a pair of exclusive boots made with exceptional quality top of mind, the Danner x Huckberry Waxed Canvas Danner Light Boots are the pair you need to shop now — and there are only 600 pairs available, so act quickly.

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.