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.


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.

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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.

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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.

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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.

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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.

Style Pick of the Week: Frye Tyler Chelsea Boots – Best Men’s Chelsea Boots for Fall

Best men's Chelsea boots for fall

Among any list of the best fall style essentials — be it one of the best fall blazers or your new go-to henley — you’d also do well to consider some of the most rugged men’s boots, right? But there’s a fine line to walk, literally, if you want to maximize your versatility. While there’s a time and a place for hard-wearing work boots, you can still get fall-minded performance and style with *drumroll please* a pair of the best men’s Chelsea boots. In fact, at the current moment, there might not be a better pair of men’s boots for fall on the market than the FRYE Tyler Chelsea Boots.

You’ve hopefully encountered the brand through its penchant for making some of the best leather boots, period, but the American heritage footwear company continues to step up its game with timeless styles like the easy-on, easy-off Chelsea boot. It all starts, of course, with quality leather when it comes to the FRYE Tyler Chelsea Boots, and in this case, we’re talking a rich Cognac leather that wears well with plenty of fall style picks (everything from dark blue jeans to black denim to olive chinos).

The FRYE Tyler Chelsea Boots — which are selling somewhat fast despite a more investment-minded price tag of $328 at FRYE — also sit atop a sturdy leather outsole for traction on slick fall streets and through day-to-night pursuits (anyone up for a park stroll and brewery visit?). Better still, the FRYE Tyler Chelsea Boots are designed for a smooth ride, thanks to the injection of a rubber forepart in the leather outsole.

The end result is a pair of sleek yet hard-wearing boots, the kind you can team with wool trousers, stretch cotton chinos or your favorite pair of blue jeans without missing a beat. On your top half, go with rugged picks like one of the best men’s henleys or keep things a touch more refined with a cool cotton blazer. Either way, be sure to get as much wear as possible out of the FRYE Tyler Chelsea Boots, because they can take it.

The Sunday Sale: Shop and Save on the Best Men’s Boots Today at HELM Boots

Best rugged leather boots for men.

As we step ever closer towards fall, and as you slowly but surely break out your collection of the best men’s boots, perhaps you’re realizing that your footwear lineup has a few pieces missing. Like, say, some rugged-yet-versatile lace-up boots from a brand like HELM Boots? Sure, the brand also makes some of the most stylish leather sneakers on the market, but it’s the best boots for men where the Austin-based company truly excels.

And that brings us nicely into our Sunday Sale. Simply hop on over to the HELM Boots Sale section to shop at least 20 percent off your new favorite pair of boots, be it the dependable, wedge-soled HELM Jakob Boots (as shown at the top of the page), the ever-versatile HELM Declan Chukka Boots, or a set of stylish sneaker boots.

Best leather lace-up boots for guys.

Whatever pair your wardrobe needs, from rugged lace-up boots to timeless chukka boots, I’d wager you’re going to find it in the HELM Sale section (and remember, you can also snag 15 percent off your first order at HELM — talk about one heck of a deal for the best on-sale boots of the moment).

Seriously, the good folks at HELM Boots can do it all, and they use methods like Blake stitched construction and handsome leathers for maximum durability and style. These styles are selling mighty quickly, so I’ll let you go early today, all the better to shop the best boots for men. See you out there this fall, my friends.

The Tuesday Steal: Save 30 Percent on the Best Chukka Boots from HELM Boots Right Now

Best leather chukka boots for men.

If you’ve been keeping up with the blog as of late, you know that it’s more crucial than ever to start gearing up for early fall with the best men’s style essentials — like the best boots for men, of course. I’ve said it before and I’ll say it again: If you can find those style essentials on sale, that’s all the better, and that brings us to the pair of rugged leather chukka boots available today at a nice discount.

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They hail from Austin’s own HELM Boots, a company you’re hopefully familiar with for its versatility and craftsmanship — they make everything from a pair of the best leather sneakers for men to some of the most rugged lace-up boots, of course.

You can add the HELM Declan Boots to that list, and you can rest even easier knowing they’re 30 percent off right now. Yes, that’s right: That discount takes these stylish leather chukka boots down below $200, a whale of deal — and a good reason to act quickly, since your new favorite chukka boots are selling fast.

Why go all in right now on the HELM Declan Boots? It’s simple, really. They’ve got all the hallmarks of dependable, durable style through and through, from a profile that’s sleek yet rugged — and wearable with slim chinos or more casual blue jeans — to the quality construction. The HELM Declan Boots are made with resoleable Blake construction (less expensive than Goodyear welting, but no less functional), and my favorite pair in particular uses handsome brown Balthazar leather that’ll get better with age.


Of course, you can also find the HELM Declan Boots in the HELM Boots Sale section in sharp Tan suede, a style that fits right in with other seasonal looks (like olive chinos, for instance). Now, sizes of the HELM Declan Boots are moving plenty quickly given that agreeable sale price of $175, so if you want a new pair of the best men’s chukka boots to call your own this fall, act now.

Style Pick of the Week: Taylor Stitch Trench Boots – The Best Men’s Boots for Early Fall

Most rugged leather boots for men.

It’s hard to believe it, but let me be the first to say: Fall is barreling towards us more quickly than you might expect, and I’ve got a few helpful style tips to set you on the path to menswear greatness. Chief among those tips: Invest in a pair of the best boots for men right now (like the rugged Taylor Stitch Trench Boots as shown at the top of the page), and then thank me later.

Those rugged leather boots are the focus of today’s Style Pick of the Week, and naturally, the brand in question knows a thing or two about making some of the best menswear. We’re talking about San Fran’s own Taylor Stitch, a longstanding favorite of your humble Brooklyn style writer.

Hopefully, you’ve got a closet packed with Taylor Stitch style essentials, be it one of the best men’s sweaters or a pair of stylish everyday pants, but the Taylor Stitch Trench Boots are a next-level style pick-up to sort out your fall footwear rotation. Let’s count the ways, shall we? They’re crafted from a handsome 4oz. Whiskey leather that’ll only get better with age, and they’re built with resoleable construction for longevity and plenty of durability, for starters.

Best lace-up leather boots for men.

The Taylor Stitch Trench Boots are also set atop a mini-lug sole from Vibram, which is designed to offer plenty of grip and traction on slick streets this fall and winter. Antique brass eyelets are a simple but durable touch, along with speed hook lacing at the top of the Taylor Stitch Trench Boots — you needn’t worry about the hardware on this pair giving out on you over time.

Better still are the smallest possible details on your new favorite pair of boots, like waxed cotton laces and natural sheepskin leather lining. Dependability and comfort are the name of the game with the impossibly cool, hard-wearing Taylor Stitch Trench Boots, which should also prove plenty versatile when it comes time to get dressed this season. Consider teaming ’em with classic Taylor Stitch chinos and your favorite Taylor Stitch shirt at the office or on the road, to name but one essential fall men’s style look.

And while it might seem a bit early to be thinking about lacing up some of the best men’s boots, it’s never too early to invest in an extremely stylish pair — the Taylor Stitch Trench Boots are just what you need now.