Tag / best men’s boots

by Beau H.

Style Pick of the Week: Rancourt & Co. Shearling-Lined Dresden Boots

Beastly boots for all of your winter adventures, folks.

There are average boots, and THEN, there are the Rancourt & Co. Shearling-Lined Dresden Boots. I’ll tell ya what, folks … Rancourt & Co. certainly knows how to get the job done, and they’ve knocked it out of the park with the Dresden Boots. They’re an absolute beast of a pair, and they just so happen to be today’s Style Pick of the Week for good reason. In fact, you might recognize ’em already — they were featured ever so recently in our roundup of the best men’s winter boots, and they’re back today … with a stylish, winter-ready vengeance. The specs and style potential of the Rancourt & Co. Dresden Boots are simply top-notch, which is absolutely what you’d expect from a brand that makes its gear with the utmost care in Maine.

In fact, the brand still largely follows the same methods they have for years, and the resulting Dresden Boots have plenty going for ’em, from the beautiful Horween leather to the rugged moc toe construction and a natural leather midsole for comfort and a touch of craftsmanship. They’re the kind of classic winter boots that evoke throwback style, with just the right amount of rugged polish.

A warm shearling lining separates these boots from the pack.

Heck, we haven’t even mentioned the shearling lining in the Rancourt & Co. Dresden Boots — that’s what really puts this pair of rugged leather boots over the top. They also feature a padded collar for perfect comfort throughout; when you need to bundle up in a snowstorm, step into these boots. The Rancourt & Co. Dresden Boots hit the nail on the head when it comes to casual weekend style, too. These are the type of boots to wear with faded denim, a classic gray crewneck sweatshirt and a stylish casual watch to grab a weekend coffee or explore your city. They’ll also pair reasonably well with business casual looks (think dark slim jeans, a navy herringbone blazer and a classic chambray shirt). And if you want to go a bit more preppy? Then style the Rancourt & Co. Dresden Boots with your new favorite vest. See? The possibilities are endless (nearly). The Reltex Lactae Hevea Rallye sole on the Dresden Boots isn’t clunky like other winter boots, yet it still provides crucial grip and a smooth ride, as the brand says. To stay on your feet on slippery roads, that functionality is key. Other finishing touches are on point, too — take the natural leather laces and the classic, handsewn moccasin construction. In short, the Rancourt & Co. Dresden Boots are everything you need in a timeless pair of winter boots — they’re wearable with everything from burgundy corduroys and a navy blazer to broken-in blue denim and a rugged henley, they look great AND they perform even better. What’s not to like?

Will the Rancourt & Co. Dresden Boots be joining your winter footwear rotation? Let me know in the comments or on The Style Guide Facebook page!

by Beau H.

Online Shopping Picks: Buy These Boots to Take on Winter in Style

There’s a heck of a lot of gear you need to take on winter in style, from the right pair of socks to a rugged henley for layering to a stylish and warm jacket. These are areas that certainly aren’t to be overlooked, and the same can be said for the boots you throw on this winter. We talked just a few months ago on The Style Guide about the best men’s boots to buy for fall, and winter calls for similarly rugged, functional style — yet with a bit of twist. Your stylish winter boots need to be able to take on blustery winds and drifting snow, and you need to be able to navigate to and from work, your favorite bar and that holiday or New Year’s Eve party. Trust me, it’s a lot … that’s why I think you’re going to dig the rugged leather boots we’ve got on tap today, from the remarkable Mark Albert Traveler Boots to a classic pair of shearling boots from Rancourt & Co. If you think I missed any brands or styles, hit me up on Twitter or drop a line in the comments below, and if you want to see how I’m wearing my boots this winter, check out my Instagram. Happy shopping!

Disclosure: This post contains affiliate links, from which a small commission might be earned on purchases. All opinions are the author’s own. Thanks for supporting the brands that support The Style Guide!

#1. Huckberry x Original Chippewa 6-Inch Service Boot — $280

Goodness gracious — Huckberry and Original Chippewa are back at it with these stellar boots.

It’s no secret that I’m a big fan of Original Chippewa and the brand’s classic Service Boots, so the Huckberry x Original Chippewa 6-Inch Service Boot is a ready-made winner in my book. These exclusive Service Boots feature a Vibram sole and a Goodywear welt for extreme traction and durability, even in the snow — and they’ll look particularly great underneath some American-made denim. Yes indeed, the Huckberry x Original Chippewa 6-Inch Service Boot is that elusive pair that can take you all around town and through the snow, then right on into happy hour.

#2. Red Wing Merchant Boot in Ebony — $320

Can Red Wing improve upon a classic? Trick question — they just did.

Is it possible to take a classic boot silhouette, one that dates back decades, and quite possibly make it better? Red Wing Heritage has done that with the Merchant Boots, a modern update to a throwback pair of boots that looks simply exceptional. The Red Wing Merchant Boots are based on a bestselling style from the brand way back in the 1920s, featuring rich mohave leather, tough brass hardware and classic Goodyear welt construction. Wear the Red Wing Merchant Boots with slim blue denim and your favorite shawl collar cardigan for timeless winter style.

#3. Mark Albert Traveler Boots (Huckberry Exclusive) — $345

A pair of boots that are stunning, stylish and just as functional as you need this winter.

We mentioned the Mark Albert Traveler Boots earlier, and with good reason. The Traveler Boots are what some might call the perfect pair of boots — if you’re into rugged, classic style. These exceedingly stylish leather boots feature full-grain Horween leather, an oil-resisting Vibram sole and the sort of construction that avoids slips and slides on snowy ground. The Mark Albert Traveler Boots even feature USA-made laces for an added dash of quality construction. Wear them with navy corduroys and a tan herringbone blazer for a blend of rugged and tailored style.

#4. Blundstone Super 550 Boots — $157.98

A unique take on the Chelsea boot from a classic brand. No complaints when it comes to getting around in the snow.

Let’s combine the look of a slightly more rugged Chelsea boot with the functionality of a dependable pair of snow boots, and … boom! The Blundstone Super 550 Boots are what you might get. The Blundstone silhouette is definitely unique and a bit quirky for some folks, but there’s no denying the traction-ready outsole and the brand’s Poron XRD sole technology. The Super 550 Boots are certainly a little more casual, and thus weekend-ready — style the Blundstone Super 550 Boots with your favorite bomber jacket.

#5. Rancourt & Co. Shearling-Lined Dresden Boot — $310.98

Rancourt & Co.

From the shearling lining to the comfortable padded collar, your feet are going to thank you for these boots.

Here’s your new favorite pair of winter boots — maybe, just maybe. The Shearling-Lined Dresden Boots from Rancourt & Co. pack a ton of winter-ready functionality into one pair of boots, from the shearling lining — of course — right down to the sturdy Lactae Hevea sole. The Dresden Boots feature plenty of warmth and style points, plus handsewn construction and that classic moc toe upper. That’s an old-school combo that makes these Rancourt & Co. boots perfect for wearing on the weekend with a classic crewneck sweater and a faded pair of dark blue denim.

#6. Taylor Stitch Cap Toe Moto Boot in Black Steerhide — $315

When Taylor Stitch makes boots, the brand does it the right way. Oh, man.

Taylor Stitch doesn’t misstep … seemingly ever, right? And that goes for when the brand puts its mind toward crafting a uniquely stylish pair of rugged men’s boots, too. Simply put, the Taylor Stitch Cap Toe Moto Boots are well worth your time and money. The Cap Toe Moto Boots are made with durable storm welt construction and feature rich black full-grain steerhide leather, and that’s not even where the good stuff ends — they come with a pair of waxed cotton laces and a pair of antique leather laces for a bit of versatile styling potential. However you end up wearing the Cap Toe Moto Boots, they’re going to treat you just fine.

#7. Hudson Shoes Fernie Boots — $240

A pair of boots that’ll help you fight the snow and look positively great when wearing a suit.

For the fella who appreciates a bit of tailored winter style to go along with weather-ready dependability, might I recommend the Hudson Shoes Fernie Boots? The Fernie Boots have been a bit of a hot seller this season, so you’ll have to act now to snag a pair — but rest assured, you’re getting a rugged and refined pair of captoe brogue boots done up in handsome brown leather. They just might be the perfect pair of boots to wear with a suit, as a thick rubber sole will help you combat the winter weather.

#8. Thorogood Beloit Boots — $229.98

Can you tell we love brown leather boots here on the blog?

Last but surely not least, I give you the Thorogood Beloit Boots, just one pair among many pairs of stylish men’s winter boots that you’re going to want to add to your shopping cart this season. Handmade in Wisconsin the right way, the Beloit Boots are about as rugged as it gets, crafted with Horween Chromexcel leather and a unique cork outsole for a comfortable fit (not to mention durable winter style). The Thorogood Beloit Boots are perhaps best worn with tough chore pants and a classic field jacket for simply getting things done this winter.

 Well, that’s one heck of a list of perfect men’s winter boots, if you ask me. I kid, I kid. And yet … from the Huckberry x Original Chippewa 6-Inch Service Boot right on through to the Hudson Shoes Fernie Boots, there’s surely something for everyone from top to bottom. If it’s dependable, workman-like style and performance you seek, try out the Thorogood Beloit Boots. Want something with a bit more edge? Take the Taylor Stitch Cap Toe Moto Boots for a spin. Need to stay extra warm and stylish? The Shearling-Lined Dresden Boots from Rancourt & Co. are your best bet. That’s just the tip of the iceberg, though — the Blundstone Super 550 Boots offer up unique looks and snow-ready toughness, while the Mark Albert Traveler Boots are practically one-of-a-kind in terms of stellar style. What’s your favorite pair on this list? Let me know in the comments below, and thanks for reading!
-Beau

 

by Beau H.

See Now, Buy Now: Step Out This Winter in the Danner x Tanner Goods Mountain Pass Boots

The right pair of boots for the winter season — and a fast-selling pair, at that!

There’s no doubt that your Style Guide team absolutely loves durable, rugged boots — especially boots like the Danner x Tanner Goods Mountain Pass Boots. You want a one-of-a-kind, stylish winter boot that performs and looks great at the same time? Perhaps some of the best men’s winter boots out there? Get these Mountain Pass Boots. You want a boot that combines the know-how and rugged style of two tremendous companies (both based in the Pacific Northwest, as it were)? Get the Mountain Pass Boots. You get the picture, right? We previously covered the Danner Mountain Light Boots on the blog — what with their James Bond-esque looks and alpine-inspired design — and the Danner x Tanner Goods Mountain Pass Boots carry with them a similar attention to detail and rugged style. It’s part of an ongoing partnership between the two brands that’ll have you reaping some serious benefits. The Vibram sole provides classic durability that you’ll surely need on slippery streets, while the suede leather upper looks cool and sleek. That’s fashion and function at work, assuredly. Yes indeed, the Mountain Pass Boots have a ton going for them.

And we haven’t even talked about the Ortho-Lite insole or the DRI-LEX lining — these aren’t a pair of old-school hikers without any technical specs. Plus, the waxed canvas collar is exactly the sort of rugged-refined detailing you might expect when a brand like Tanner Goods — renowned for the quality of its leather — gets in the mix with Danner. Of course, the resulting Mountain Pass Boots are the complete package, able to work with dark denim and a crewneck sweater or alongside burgundy corduroys and a denim trucker jacket. Now, all you need is a pair of stylish winter socks and maybe, just maybe … a rugged flannel shirt. Sounds like the perfect outfit for an afternoon spent by the fire or at your favorite brewpub, yes? Who’s with me on that?

Will the Danner x Tanner Goods Mountain Pass Boots be finding their way onto your feet this season? Let me know in the comments or via Twitter! 

 

 

by Beau H.

Style Pick of the Week: Nisolo Andres Boots

Nisolo Andres Boots

Your new favorite pair of black leather boots? It’s very likely, my friends.

There are your regular, everyday boots — which we certainly know and love here at The Style Guide — and then there are supremely stylish men’s boots like the Nisolo Andres Boots, today’s long-awaited Style Pick of the Week. I’m definitely a fan and a proponent of rugged leather boots, especially in the fall and winter months, and it’s refreshing to find a pair of classic leather boots that deliver in terms of both looks and functionality — Nisolo absolutely gets that right when it comes to the Andres Boots. We — and by we, I mean your editorial team of one — love the work being done by Nisolo on all fronts, from stylish boots to the durable, handsome Nisolo Leon Weekender, If  you’re not yet familiar with the brand, I’d advise you listen up … and possibly get your credit card handy when it comes to the Nisolo Andres Boots. Notably, these boots combine a sleek silhouette with weather-ready capability via a water-resistant leather upper. Are they among my picks for the best men’s boots for winter? You betcha. And if you’ve been paying attention to the classic boots normally featured here on The Style Guide, they’re unique in another way, as well … namely, the Nisolo Andres Boots are done up in black leather, a change of pace from my *ahem* “obsession” with rugged brown leather boots. So, if you’re on the hunt for a stylish pair of black leather boots, give the Andres Boots a fair shake, my friends.

Nisolo

A slim profile, quality construction and plenty of weather-ready functionality from the Nisolo Andres Boots.

The Andres Leather Boots have a ton going for then, and again, that’s coming from a guy who’s much more partial to brown leather boots. It’s helpful, then, that Nisolo Andres Boots also come in … you guessed it … handsome brown leather. But for style that’s sleek, sharp and just a bit more ready to wear with sharp tailoring this season, the Nisolo Andres Boots in black leather should be your pick. The Andres Boots are certainly a unique change of pace, combining the silhouette of a crisp dress shoe with the tough outsole of a boot — and that means you can wear these with slim black denim, grey corduroys or navy wool trousers in equal measure. The Andres Boots are also the sort of footwear that’s going to elevate even more casual outfits, like a crewneck sweater and broken-in denim. And when you want to navigate slippery terrain to head to the office, layer up with a tan herringbone blazer, grey flannel trousers and … the Andres Boots, but of course. Are you a newfound fan of the Nisolo Andres Boots or a longtime Nisolo supporter? Let me know in the comments below — enjoy fall and winter, my friends!

Thanks for reading,

-Beau

 

by Beau H.

See Now, Buy Now: Invest in the Rancourt & Co. Wolf Boots for Your Next Fall Adventure

A dependable, durable pair of Horween leather boots finished with a Vibram rubber sole — Rancourt & Co. knows how to make ’em the right way.

Over the past few weeks here at The Style Guide, we’ve admittedly talked a ton about rugged fall style, from the best men’s boots to durable outerwear to stylish fall shirting — but we’ve got more on the way today. Our latest recommendation when it comes to dependable fall style? The investment-quality, USA-made Rancourt & Co. Wolf Boots, available in time to close out fall and head into early winter (gulp) in style. An exclusive made just for Huckberry to commemorate the brand’s 50th anniversary, the Wolf Boots from Rancourt & Co. are made to last at least that long (no matter how hard you wear  ’em).  The brand has certainly pulled out all the stops to craft a one-of-a-kind pair of boots, starting with Chromexcel bark-tanned leather and finishing with handcrafted construction by the Rancourt team. We’d be remiss not to mention the waxed laces and metal eyelets, too. That’s just the tip of the iceberg, though.

Just like the Rancourt & Co. Carson Low Sneakers — a fitting pair of fall kicks in their own right — the Wolf Boots are as easy to wear during the work week as they are on the weekend. With details like Blake welt construction and cap toe stitching for durability, you can be sure they can take a beating. The Vibram rubber mini lug sole also provides grip and toughness to brave the elements this fall and winter. I’d wear them with a rugged overshirt and slim black denim to head to a brewery — a favorite pursuit of mine. For day trips and fall or winter hikes, the Rancourt & Co. Wolf Boots are also going to take you the distance.  Even during the work week, the Wolf Boots should be in your rotation. Now, maybe your closet is already packed full of tough boots … but it can’t hurt to add one pair, can it? Not when that pair is as stylish, dependable and well-made as the Rancourt & Co. Wolf Boots.

Will these Rancourt & Co. boots be heading your way soon? How would you style them?

by Beau H.

See Now, Buy Now: Step Up Your Boot Game with Beckett Simonon’s Dowler Cap Toe Boots

Beckett Simonon

Sleek, sharp and well-made leather boots from Beckett Simonon.

Folks, the latest entry in our See Now, Buy Now series has me seriously excited for cold weather, the perfect time to break out some of the best boots for men. We’re talking, of course, about the stellar, stylish and refined-yet-rugged Beckett Simonon Dowler Cap Toe Boot as seen at the top of the page. You should surely know Beckett Simonon  from an earlier entry in our See Now, Buy Now series — the brand specializes in premium, stylish men’s footwear, from sharp wingtips to the rugged cap toe boots on display today. The Dowler Cap Toe Boots really do have a lot going for ’em, from the Blake construction that adds durability to the beautiful leather quality. They’re also carefully handmade — part of the reason you’ll have to pre-order the Dowler Cap Toe Boots now, then wait until January 2018 until they ship. That wait, though? It’s definitely worth it.

You certainly get a lot of variety for the price — the Dowler Cap Toe Boots also come in Black Calfskin Leather and Tan Calfskin Leather. I’m partial to the Brown Calfskin Leather option shown here — they’d be an excellent way to complement to everything from slim dark blue denim and a heather grey shawl-collar cardigan to an American-made Oxford and charcoal trousers. Heck, you can even wear the Dowler Cap Toe Boots with your favorite henley and grey denim for a bit of rugged edge. And sharp winter tailoring is going to look great alongside these sleek Dowler Cap Toe Boots — think a navy worsted wool suit or a grey flannel three-piece suit. I’m telling you, the Dowler Cap Toe Boots can really do it all — pre-order now and see for yourself, yes?

Will you be buying the Dowler Cap Toe Boots from Beckett Simonon ? Drop me a note in the comments or on Twitter! 

by Beau H.

See Now, Buy Now: Astorflex Is Making Your New Pair of Fall Chukka Boots

Astorflex

Sleek leather chukka boots crafted for durability and style all season.

We talk a lot about stylish leather boots here on The Style Guide. Specifically, we’ve talked a lot about rugged, stylish Astorflex footwear this fall season. The Astorflex brand can do it all, from classic suede chukka boots to Chelsea boots and lace-up boots, and they craft products with quality and sustainability in mind. And now, Astorflex  has definitely done it again — meet your new favorite pair of leather chukka boots. That’s certainly high praise, but stick with me for a second. The all-new, Huckberry-exclusive  Astorflex Greenflex Leather Chukka Boots are where it’s at this season — to put it simply.  You might already be familiar with the Astorflex Greenflex Chukka Boot in its original iteration — finished with stylish and sustainable suede. But the Greenflex Leather Chukka Boots from Astorflex up the ante considerably, starting with durable tan leather that’ll pair up nicely with fall favorites ranging from slim blue denim to grey corduroys or olive chinos. Yes, that’s right — they can work with #menswear combinations aplenty (including charcoal trousers like the Flint and Tinder 365 Pant as seen above).

That wearability starts with the premium construction of these stylish men’s boots, because you can’t rock leather chukka boots for days on end without a sturdy build. And the leather sole and stacked leather heel guarantee tough durability. Using soft European leather and the sort of handmade construction you can only find in northern Italy also guarantees great quality.  Yes indeed, the Astorflex Greenflex Leather Chukka Boots check all the boxes when it comes to a go-anywhere pair of durable leather boots. Feel free to wear these now with broken-in blue denim and a striped henley on the weekends, then keep them handy as you dress for fall travel or even a day at the office. The slim profile and handsome tan leather of the Astorflex Greenflex Leather Chukka Boots will team nicely with navy or light grey wool trousers and a navy blazer — plus an American-made Oxford — for meetings, presentations and drinks after work. Given all of those possibilities, how are you ever going to take the Astorflex Greenflex Leather Chukka Boots off? I’m not quite sure , to be honest.

Will the Astorflex Greenflex Leather Chukka Boots be joining your ever-growing footwear collection this fall? 

by Beau H.

Style Pick of the Week: Wolverine Original 1000 Mile Boots

A classic in any season — especially fall.

Folks, let’s dive on into another Style Pick of the Week. More specifically, let’s talk rugged fall boots — as in the standout Wolverine Original 1000 Mile Boots. They’re investment-worthy and wish list-worthy, to say the least. Surely, if you’re a #menswear fan and have kept up with the industry, then you’ll recognize the durable, classic and resurgent style of the Wolverine 1000 Mile Boot. They were a trendy favorite in the mid-2000s as workwear and made-in-America goods surged back into play, but here’s the catch — Wolverine has made these boots a modern-day classic. Yes, the handsome, rugged and timeless silhouette of the Wolverine Original 1000 Mile Boot is just as relevant today. And what better season than fall to break out a pair of classic leather boots, after all? Wolverine has come up in the past on The Style Guide, specifically when talking the best boots for fall. Why not get ready for the season with the real deal, the Wolverine 1000 Mile Boot? Ehh? Yessir, Wolverine has nearly outdone themselves once again with this easily wearable, ridiculously well-crafted silhouette — and again, the time is just right to pick up the 1000 Mile Boots, my friends. And if I were you, I’d wear them to your next tailgate, on a bar crawl or to the office when paired up with a stylish fall blazer. They’re that good.

A tough silhouette that’s not too bulky — wearable with jeans or wool trousers in equal measure.

Like other Style Guide favorites — including the Original Chippewa Service Boots — this pair of 1000 Mile Boots is built to last right here in America. Wolverine uses uncompromising standards in crafting boots that can work with every single one of your fall menswear essentials, from rugged dark blue denim and a light blue denim shirt to faded black denim and a slim striped henley — and that’s only the beginning. The thing with the Wolverine Original 1000 Mile Boots  is that they’re only going to get better the more you wear them. Heck, the pattern of the boots itself is recreated from 1914, when the original 1000 Mile Boots  launched. And the leather?  It comes from Horween, perhaps the country’s foremost leather crafters. Throw in well-considered details like flat waxed laces and a leather outsole, and you’ve got a stunning pair of boots that can certainly last … beyond a thousand miles. See what I did there? At any rate, the craftsmanship and rugged appeal of the 1000 Mile Boots keeps going and going. OK, we’re done now. Thanks for reading!

Will the Wolverine Original 1000 Mile Boots be making their way into your footwear rotation this fall? How would you style the 1000 Mile Boots?

by Beau H.

Online Shopping Picks: The Best Men’s Boots to Buy This Fall

My friends, it’s that time of the season again — time to talk about the best men’s boots to buy for fall. The season is, as I’ve said in past weeks, perhaps the best for us #menswear fans — particularly if you’re a fan of rugged fall style essentials. We get to break out our favorite layers, from a slim denim trucker jacket to a rugged striped henley, and better yet … we get to break out stylish leather boots aplenty all along the way. A great pair of leather boots can complement nearly any outfit, and I think you’ll find that the picks below do just that. A herringbone blazer and slim dark denim? Throw on a pair of classic leather chukkas. A casual striped henley and grey selvedge denim? Stylish suede boots ought to do the trick. And that’s just the tip of the iceberg when it comes to the below picks.  Again, the right pair of leather boots  — affordably priced, well-made and supremely stylish — can take you from football tailgate to bar crawl and back, with a week of work in between, of course. So, start checking a few items off your men’s style wish list this season; I know I’ve got a few more picks to add to mine. Follow along on Instagram for real-time style updates, and let me know how we’re doing over at The Style Guide Facebook page.

#1. Original Chippewa 6-Inch Service Boot in Crazyhorse — $270
Original Chippewa

A not-too-bulky pair of rugged fall boots featuring durable construction and great looks.

Believe you me, it’s tough to play favorites when it comes to rugged leather boots for the fall season — but Original Chippewa just might take the cake when it comes to the  brand’s 6-Inch Service Boot. With a rugged silhouette that’s not too bulky — plus premium construction and a quality price — the 6-Inch Service Boot is darn near the whole package. Wear it with your favorite pairr of dark denim and a black moto jacket for edgy weekend fall style.

#2.  Hudson Shoes Elmore Boot in Black — $270

A sleeker, modern combat boot with plenty of style to burn.

Fancy something a little more sleek and less rugged? Hudson Shoes has what you’re looking for when it comes to the Elmore Boot. With the look of a classic combat boot, the Elmore Boot should lend itself well to rock n’roll-ready outfits — think slim, faded grey denim and a stylish graphic tee. The slick black color also lends itself to dressier pairings — if you’ve got a tan or grey herringbone suit in your rotation, the Hudson Shoes Elmore Boots are the boots with which to wear it.

#3.  Astorflex Bootflex in Dark Khaki — $190
Astorflex Bootflex

A rugged-yet-comfortable pair of lace-up boots.

Long a favorite around these parts for blending sustainability and great looks, Astorflex has been making — in recent months, anyways — what could just be your new favorite pair of boots — the Astorflex Bootflex in Dark Khaki.  Finished with a natural rubber sole for comfort and done up in a versatile shade of deep tan, the Astorflex Bootflex should work quite stylishly for plenty of casual fall outings — from the pumpkin patch to your next football tailgate.
#4. Red Wing Iron Ranger Boot in Harness — $300

As good as it gets — the legendary Iron Ranger Boot from Red Wing. Bravo, folks!

As legendary a pair of fall boots as it gets, Red Wing absolutely delivers the goods when it comes to its lauded Red Wing Iron Ranger Boot. Blame it on the Americana craze of the mid-aughts, but the Iron Ranger Boot has taken on a life of its own — and with good reason. It’s a ridiculously rugged, stylish and wearable boot that’ll break in beautifully over time. What’s not to love about that? A job well-done to Red Wing on this one.

#5.  Hudson Shoes Leiwston Chukka — $110

A sleek pair of chukka boots, made with versatile style in mind.

We’ll throw some classic leather chukka boots in the mix this time, just for fun (wink, wink). As first seen in our Style Pick of the Week series, the Hudson Shoes Lewiston Chukka blends a truly excellent price with quality craftsmanship and versatile style. These stylish leather chukka boots — this pair is an admittedly popular seller — can team with nearly anything in your wardrobe, from a worsted wool navy suit, a pair of slim grey denim or a faded pair of blue jeans.

Honorable Mention: Astorflex Greenflex Rough in Sand — $150

An updated take on the Astorflex Greenflex — the durable, treaded sole is a key point of differentiation.

As previously seen in this site’s See Now, Buy Now series, the Astorflex Greenflex Rough is a recent addition to the brand’s line of stylish and sustainably made boots (but you know all about those already). And the Greenflex Rough updates the classic suede chukka in a few crucial ways, starting with the durable sole featuring a treaded grip. It’s a neat tweak on a pair of boots that’ll work with broken-in denim, olive chinos or burgundy corduroys this season.

That wraps up our take on the season’s best boots, folks. What did you think? Any particular favorites on this list? Again, the versatility and rugged appeal of a pair of boots like the Astorflex Greenflex Rough can’t be emphasized enough — and a classic pair of tough leather boots like the Red Wing Iron Ranger certainly deserves its place on this list, too. Don’t forget the casual, versatile look of the Astorflex Bootflex, too — that’s one pair that you can put a lot of miles on this fall. And if it’s sleek fall style you prefer, the Hudson Shoes Elmore Boots are the ones to buy. Let me know in the comments below or on Twitter as to your favorite style — see you out there this fall!

-Beau

by Beau H.

See Now, Buy Now: Huckberry Is Now Stocking Your New Favorite Chukka Boots

A dependable pair of chukka boots, now available on an upgraded tread sole. Get ’em ASAP via Huckberry.

Some pairs of footwear just immediately call to mind the season ahead — right now, the new Astorflex Greenflex Rough Boots are that pair of footwear (at least, to yours truly at The Style Guide). And the great news? You can get your new favorite chukka boots right this very instant from our pals at Huckberry (Editor’s note: Huckberry is an advertising partner of this blog — but all opinions are my own!). What exactly is it that makes the Greenflex Rough an excellent addition to your fall footwear rotation? Take it from me — this new Astorflex style knocks it out of the park when it comes to a combination of classic looks and seasonal reliability. And if you haven’t started shopping for your fall style essentials yet, I’d urge you to start with the Greenflex Rough. I certainly love Astorflex for its mix of sustainability, style and versatility, as you might remember from our Style Guide Recommends series. The Astorflex Greenflex, absolutely a classic pair of chukka boots, is a particular favorite in that regard — and the Greenflex Rough amplifies those qualities even more. Crucially, Astorflex amps up this silhouette in casual, rugged fashion, starting with a treaded sole for added grip and traction on slippery surfaces this fall. Throw in metal eyelets for durability, and the Greenflex Rough is a winner. The good —  neigh, excellent — part about this approach is that the Greenflex Rough still retains all the style points you need this fall. So how should  you wear the Greenflex Rough? Bear with me.

Crucially, the Greenflex Rough comes in a rich Sand colorway, all the better for pairing with everything from slim black denim and a classic men’s T-shirt to slim olive chinos and a rugged henley. Don’t save them simply for rugged fall style situations, though. I’d break out the  Astorflex Greenflex Rough Boots with an unstructured navy blazer, a classic grey crewneck sweater and burgundy corduroys for a little late fall, business casual style when the time comes. Don’t worry if they can stand up to repeated wear, either — from the looks of it, the Astorflex Greenflex Rough Boots are built for the long haul this season.

How would you style the Astorflex Greenflex Rough Boots? Will you be picking up this new addition to the Astorflex line?