See Now, Buy Now: The Red Wing Heritage Classic Chukkas Are the Perfect Winter Chukka Boots

Rough and tough chukka boots from an iconic branda.

Check your calendar. And now look at the boots you’ve got on. Are they a stylish pair of leather boots for winter? Better yet, are they the Red Wing Heritage Classic Chukkas? No and no? Well, let’s fix that today via the latest entry in our See Now, Buy Now series. Here at The Style Guide, your author loves a classic, iconic brand like Red Wing Heritage for reasons aplenty, chief among them being the brand’s ongoing commitment to timeless styles and seriously tough construction. Those are both qualities that are going to serve you well this winter. And the Red Wing Heritage Classic Chukkas in particualr just get the job done, to say the very least. Finding the right pair of winter boots is a tricky endeavor in more ways than one — you want a pair that can stand up to snow and slush, yet you’re also going to need to be able to wear them in a myriad number of style situations (as you dress for the office or head to your favorite brewery, in particular). Again, the Red Wing Heritage Classic Chukkas deliver.

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SHOP: The Red Wing Heritage Classic Chukkas via Bespoke Post 

Of note, they channel the same timeless construction and quality for which Red Wing Heritage is known, and the brand’s Minnesota roots sure do come in handy — the Red Wing Heritage Classic Chukkas feature an Atlas Tred outsole, plus nickel eyelets for durability throughout the chilly winter. While you might be better off wearing the Huckberry Duck Boots in an extreme blizzard, the Red Wing Heritage Classic Chukkas are as good as it gets the rest of the time. The plain toe chukka construction and briar oil slick leather are two touches that stand out subtly and stylishly, making them an easy bet to wear with everything from expertly faded denim and a grey crewneck sweater to your favorite henley and a tough waxed trucker jacket.
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Of course, the Red Wing Heritage Classic Chukkas can also be dressed up ever so slightly — try them with the Billy Reid Bond Peacoat, plus a classic Oxford shirt and slim tan chinos, for Sunday brunch or even a day at the office. Yes, Red Wing Heritage boots can work at the office — it’s possible, folks. Good luck out there, and let me know on Twitter if these boots work out for you.

SHOP: The Red Wing Heritage Classic Chukkas via Bespoke Post 


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See Now, Buy Now: The Red Wing Heritage Classic Moc Boots Are the Perfect Winter Boots to Buy Now

Red Wing Heritage

Rugged boots that’ll last all winter.

On the hunt for the perfect winter boots? Yes, that’s right — we said “perfect.”‘ Perfection is a very high bar to clear, admittedly, and yet there are certain brands, like Red Wing Heritage, that continue to strive toward that aim by sticking to what they know best. Now, we previously talked about the Red Wing Heritage Classic Moc Toe Boots as seen at the top of the page (in this post), but we’re back again to dive deeper today — they’re just that good. That’s surely lofty praise, but a classic brand like Red Wing Heritage can back it up — and it’s all the better that the Red Wing Heritage Classic Moc Toe Boots are but the latest release from the lauded company to land on your wish list of men’s style essentials. That’s what your humble author thinks, at least. Why’s that now?

SHOP: The Red Wing Heritage Classic Moc Toe Boots
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Well, my friends … the Classic Moc Toe Boots from Red Wing fit right in with the brand’s lineup of stellar boots … yet they stand out quitely in their own, very pleasing way. Much like the equally rugged and winter-ready Red Wing Heritage Rover Boots, the Classic Moc Toe Boots are made to lace up and get to work, starting with the Traction Tred wedge outsole for durability and grip on icy winter surfaces. The use of Goodyear welt construction also adds another dimension of toughness — yes indeed, these could be the  perfect winter boots.

And lest you expect anything but the best from Red Wing Heritage, these rugged moc toe boots are made with … yes, you guessed it — the brand’s iconic full-grain, oil-tanned leather, fashioned here into an incredible pair of everyday boots that you should wear as much as you can. What are my recommended pairings for the excellent Red Wing Heritage Classic Moc Toe Boots? That’s pretty easy, I think. Start with expertly faded slim blue denim, add a classic henley and throw on a rugged shawl cardigan.

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Or wear these boots with classic everyday chinos, a timeless chambray shirt and of course, an heirloom-quality peacoat. The details and construction are simply applause-worthy, meaning you should wear them all that much more. Heck, you can even try the Red Wing Heritage Classic Moc Toe Boots with a tailored charcoal flannel suit and a chambray dress shirt. Yes, yes you can — no doubt about.

Thanks for reading! Are these stylish leather boots making their way onto your feet this season?

SHOP: The Red Wing Heritage Classic Moc Toe Boots

 

Style Pick of the Week: Red Wing Heritage Rover Boots

Timeless, durable leather boots that pass every test you could throw at ’em. Image courtesy of Red Wing Heritage.

Let’s keep it simple to start today’s Style Pick of the Week off the right way, folks: For fall, you need nothing less than the Red Wing Heritage Rover Boots on your feet. After all, if you’re going to snap up a pair of stylish leather boots just in time for the season, you might as well make ’em the best of the best.  And if you read the blog at all, you’re aware that we’re all about quality, timeless materials and a distinct sense of versatility & toughness — all of which Red Wing Heritage stands by. And the Rover Boots in particular sit right in the crosshairs of what you should be looking for this fall — boots that simply won’t quit, the kind that’ll pair with your favorite dark denim and a flannel shirt or a thermal henley for weekend (and weekday) adventures aplenty. They’ll work with more outdoors-minded pieces like tough chore pants and a rugged flannel-lined trucker jacket, too. What separates the Red Wing Heritage Rover Boots from the rest of the pack?

SHOP: The Red Wing Heritage Rover Boots and Red Wing Basic Care Product Kit  

It’s simple: The same approach and attention to detail that makes any pair of boots from the brand tough to beat. The best boots for fall start with the best leather, and Red Wing sits at the top in that category — they make it look easy with full-grain, oil-tanned leather from their own Minnesota tannery. Goodyear welt construction, a process that allows the boots to be resoled after years of hard wear, also, sets the beautifully rugged Red Wing Heritage Rover Boots apart from the pack.

Red Wing Heritage

Another look at the workman-like profile of these tough leather boots.

The construction of these boots is notable for another reason — they’re, somewhat incredibly, water, stain and perspiration-resistant — yep, the Rover Boots are as tough and stylish as it gets. You’re also riding easy in terms of comfort: These durable boots are built from the ground up with a crepe rubber sole. So, you know they can stand up to most anything. Might I also suggest you snag a handy Red Wing product care kit to keep the Rover Boots looking fresh? That’ll do it. Heck, even the price is a selling point when it comes to the Red Wing Heritage Rover Boots — try finding a pair of boots like this for under $300 anywhere else. It’s tough to do, yes? I think you’ll agree with me when I say the Red Wing Heritage Rover Boots are all you need for fall, right down to the USA-made construction. Who else is ready to break out these handsome, rugged and stylish boots? I thought so. If you pick up these boots, keep me posted on Twitter. And thanks for reading!

SHOP: The Red Wing Heritage Rover Boots and Red Wing Basic Care Product Kit  

See Now, Buy Now: The Red Wing Iron Ranger Boots Are A Must-Have Classic for Fall

Red Wing Iron Ranger

An incredibly high-quality, long-lasting pair of stylish men’s boots from Red Wing Heritage.

Are there certain items, certain menswear essentials, that are truly timeless and averse to trends? In short: Yes. And my friends, the stunning Red Wing Iron Ranger Boots fall squarely in that camp — they’re absolutely one of the best pairs of men’s boots to buy now, and hopefully … for forever. That’s saying quite a lot, but there’s a reason they’re part of our ongoing See Now, Buy Now series: If I were, I’d buy the Red Wing Iron Ranger Boots right this instant. Durable leather boots like these are but one way to start getting ready for fall — so much of the fall season revolves around getting the details right in terms of fit, texture & rugged appeal, and the Red Wing Iron Ranger Boots have got all of that, and then some. They’re a timeless pair of boots for a reason: The silhouette is at once recognizable, functional and seriously stylish, and the specs on the Red Wing Iron Ranger Boots are investment-worthy. From the use of rugged Hawthorne Muleskinner leather — guaranteed to get better with age — to the Goodyear welt construction, these stylish leather boots have it all.

And the great thing about a durable, versatile pair of leather boots for fall, like the Red Wing Iron Ranger Boots? You can wear ’em with plenty of style essentials for the season. Take an indigo denim shirt and slim black denim, then add the Iron Ranger Boots, for instance — you’re ready for a night at your favorite brewpub or a rock show in equal measure. As far as other ensembles go, the Red Wing Iron Ranger Boots can pair up nicely with more rugged favorites, like a grey crewneck sweater, a thermal henley and tan chinos. See? Versatility at its finest. Heck, if you were feeling quite adventurous, I’d say you should trot out the Red Wing Iron Ranger Boots with a navy cotton blazer (like the Taylor Stitch Everyday Blazer) and a white Oxford if you work in a more casual office. Yessir — the Red Wing Iron Ranger Boots can do it all, nearly.

OK, let’s hear it — what are your thoughts on the Iron Ranger Boots? Are they on your fall style wish list?

Online Shopping Picks: The Best Men’s Chukka Boots for Fall

Editor’s note: For a full set of menswear shopping picks, click that link.

If you’ve followed along with The Style Guide since the very beginning (way back in 2013, folks), you might recall your author extolling the virtues of certain style essentials. Although there are basics like a classic blue Oxford and slim dark denim  for your top half, those essentials can be a bit more difficult to pin down in terms of footwear. Or are they? One of those key pieces is absolutely the chukka boot. Versatile, durable, wearable no matter the weather. That being said, there’s no better time to get your footwear wardrobe refreshed (or started, or added onto) than during the fall. It’s perhaps the best time of the year for menswear, what with layering and rugged textures galore — and even if you live in a temperate climate, maybe you’ve got a special place in your heart for today’s topic: The best men’s chukka boots for fall. The time just feels right to dive into a bevy of boots that can exude style both rugged and refined, dressy and casual. That’s darn near the definition of a style essential, and it’s as good of a place to start as any in today’s latest menswear shopping picks entry. Of course, there are all kinds of other boot styles out there for fall and winter (wingtip boots, anyone?), but rest assured we’ll get to those in good time. Want to see how to style chukka boots? Head to Instagram or search this site’s archives (or heck, head on over to Twitter, too).

#1. Thursday Boots Whiskey Scout Boot — $149

A rich pair of brown leather chukkas practically made for fall.

A rich pair of brown leather chukkas practically made for fall.

Having tried everything from the much-loved Roughout Captain Boot to the dependable Suede Scout Chukka, this #menswear writer can definitely vouch for the value inherent in Thursday Boots’ footwear assortment. Checking out the Brown Scout Chukka during a spring trip to Washington, D.C. sealed the deal for me as far as the brand’s chukkas go, and it’s very safe to assume that the rich Whiskey Scout Boot will perform much the same. The color is, quite simply, handsome and very wearable with everything from crisp olive chinos and a cream cable sweater to a worsted wool suit. For the price, that’s applause-worthy.

#2. JackThreads Mac Desert Chukka — $80

A new footwear introduction from a brand that can do just about everything.

A new footwear introduction from a brand that can do just about everything.

It might not surprise you to read that JackThreads made an Online Shopping Picks entry on this site. However, what might come as a shock is that the much-loved E-commerce retailer now has a line of footwear to back up the rest of its affordably priced, stylish menswear line.  Let’s start with the important stuff. First off, that combination of looks and price — can’t beat it. $80 for a chukka that bears the JackThreads name is A-plus, truly. The lower profile, Taupe colorway and crepe sole make them the ideal weekend chukka — pair them with a broken-in pair of blue denim and a crewneck sweater for a put-together casual look, or mash them up with slim wool trousers and a navy cardigan to head back to the office. Oh, and pick up a second pair while you’re at it — did we mention the excellent price?
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#3. Johnston & Murphy Copeland Chukka — $155

Equal parts casual and sharp.

Equal parts casual and sharp.

If the Thursday Boots chukka seen at the top of the page is a dressy chukka boot, and the JackThreads chukka boot seen here above is a casual chukka boot, the Johnston & Murphy Copeland Chukka is something of a hybrid. Featuring  a deep red-brown oiled nubuck that should break in beautifully, the contrast stitching and crepe sole give it a casual feel. But make no mistake, this is a still a dependable leather chukka boot you should pair up with navy suit trousers and a grey cardigan, or a broken-in pocket tee and dark denim for weekend errands.
Buck Mason - Timeless Design. Made in America.

#4. SWIMS Barry Chukka in Taupe/Biscuit — $230

Casual, reliable and waterproof, all at the same time.

Casual, reliable and waterproof, all at the same time.

Chukka boots that offer a little bit of everything are nice to have on-hand — especially if your fall adventures take you everywhere from a football game to park hikes to pumpkin patches (yes, we’re going there already). In particular, these SWIMS chukka boots are fully waterproof, and combine the styling potential of a casual crepe sole with the functionality needed for tricky fall weather. The silhouette feels more like a sneaker than a classic chukka boot, and that’s not a bad thing — this pair would work especially well with burgundy corduroys and a long-sleeve merino tee for aforementioned weekend adventures.

Related: The Best Suede Chukka Boots to Buy Right Now

#5. Red Wing Heritage Weekender Chukka — $230

A unique chukka boot that works for both spring and summer style scenarios.

A unique chukka boot that works for both spring and summer style scenarios.

If you perused the pages of this site back in July, you’re familiar with the Red Wing Heritage Weekender Chukka. It’s a lighter-weight chukka boot that works equally well in the spring and summer as it does during the fall and winter — that makes it worth the price alone. It’s a new addition to the Red Wing Heritage line that plays off the brand’s rugged heritage while offering up a bit more flexibility and comfort than a thick-soled pair of winter boots. We’ll get to that point in the season eventually, but for now, know that you just might have a chukka boot fit for adventures seven days a week — and then some. They’re the ideal complement to classic navy chinos, and they’ll put in plenty of hours beneath trusty dark denim and a slim fall flannel shirt.

Did the above list of the best men’s chukka boots get you thinking  a bit? A trusty pair of chukka boots can seriously become a multi-day workhorse in your footwear arsenal, easily wearable with business-casual or weekend-casual outfits. Embracing the changing seasons can be a whole lot easier if you have the right gear to wear, too. That certainly starts with a rugged, dependable pair of chukka boots – after all, there really aren’t too many fall-centric outfits that don’t start with a great pair of boots (or maybe that’s just your author’s opinion). And with such great variety on the market — from a fresh style done by a heritage brand to an entirely new E-commerce offering from JackThreads — there are plenty of picks worth exploring. Want to share your own? Leave a note in the Comments section below!

Until our next menswear shopping picks post — coming next week — stay tuned for the Friday Read, and stay stylish.

-Beau

Rolling the dice: Heading West for Liberty Fairs Las Vegas

Editor’s note: To recap the last time I hit the road, click here.

A hot and sunny business trip to Las Vegas. Ivy Blazer by Grayers. Pocket square by J. Crew. Denim Shirt by JackThreads. Slim Stone Chinos by Taylor Stitch. Chukkas by Timberland. Mod Watch by Timex x Todd Snyder.

A hot and sunny business trip to Las Vegas. Ivy Blazer by Grayers. Pocket square by J. Crew. Denim Shirt by JackThreads. Slim Stone Chinos by Taylor Stitch. Chukkas by Timberland. Mod Watch by Timex x Todd Snyder.

Out of all the things that excite me about New York City and the chance to work in the menswear industry, there are certain parts of the job that just can’t be beat. Although I certainly hope to do a lot more, I’m pretty thankful and lucky right now that I get the chance to travel for my day job, and blog about that travel, at the same time. Such was the case these past four days , as I headed west to Liberty Fairs in Las Vegas; it’s a twice-yearly men’s fashion trade show that makes stops in NYC and Las Vegas, showcasing what’s new and next in the industry. That means everyone from fashion magazine editors to publishers, bloggers and sales representatives are gathered under one massive roof to scope out seasonal trends, post relentlessly on Instagram and of course, do business — everything from socks to shoes to outerwear is on display by brand. It’s a busy, hectic time, which didn’t leave much opportunity to sight-see. Although I experienced a bit of the bustle during New York Fashion Week: Men’s, hitting the road to travel and check out Liberty Fairs in a city like Las Vegas was another animal entirely. As always, that’s why I hauled my favorite #menswear essentials with me.

Travel essentials fit for Vegas. Voyager Waxed Weekender by Owen & Fred. T-shirt by Public Rec Apparel. Capital Shorts by OLIVERS Apparel. Adventure Log by Word Notebooks. Mod Watch by Timex x Todd Snyder. Sunglasses by Steven Alan Optical. Belt by J. Crew. Lanyard by Tanner Goods.

Travel essentials fit for Vegas. Voyager Waxed Weekender by Owen & Fred. T-shirt by Public Rec Apparel. Capital Shorts by OLIVERS Apparel. Adventure Log by Word Notebooks. Mod Watch by Timex x Todd Snyder. Sunglasses by Steven Alan Optical. Belt by J. Crew. Lanyard by Tanner Goods.

As I’ve been on the road a lot lately, my durable, rugged Owen & Fred Voyager Waxed Weekender has gotten a lot of work — and for good reason. If you don’t have a stylish weekender bag, and you’ve instead been relying on an old suitcase or a gym bag, making the switch is a mighty good investment. Unlike a recent trip to Michigan for a bachelor party, Las Vegas presented quite the different set of challenges — that would be the extreme heat, of course.  Standard, sweat-wicking materials just wouldn’t do, though. With style in mind, I was happy to test out a new T-shirt from Public Rec Apparel. Known for its All Day Every Day Pant, the brand recently launched a super-soft, super-comfortable and super-durable T-shirt. The tee is made with a remarkable sweat-wicking fabric blend in a  silhouette that still looks smart on its own or under a blazer — you can’t say that about your standard gym wear.  And that tee was complemented nicely another staple that merges athletic performance materials with a tailored silhouette. Yes, the OLIVERS Apparel Capital Short was just the right pair to wear from New York and right into the Vegas heat — the shorts feature a nylon-spandex blend & four-way stretch, yet fit and looks like a pair of slim chino shorts. Those two pieces kept me comfortable, which was crucial for a long travel day.

A Monday of meetings and menswear. Pocket Tee by Steven Alan. 505C Jeans by Levi's. Ivy Blazer by Grayers. Mod Watch by Timex x Todd Snyder. Chukkas by Timberland. Striped socks via the latest SprezzaBox. Notebook by Word Notebooks.

A Monday of meetings and menswear. Pocket Tee by Steven Alan. 505C Jeans by Levi’s. Ivy Blazer by Grayers. Mod Watch by Timex x Todd Snyder. Chukkas by Timberland. Striped socks via the latest SprezzaBox. Notebook by Word Notebooks.

With my accommodations all set and a busy slate of trade show appointments locked in, it was time to hit the ground running on Monday. Throughout the course of a busy two days, it was excellent to be able to catch up with some great blogger friends like Leo of Levitate Style and Danielle of She’s A Gent. The duo was among a group participating in The Studios at Liberty Fairs, a partnership giving creatives the chance to create content — everything from photos to videos, portraits and social media posts — with brands and fellow influencers across three very busy days at the trade show. So given the need to look camera-ready, I tried to rise to the occasion while fighting the heat. A soft Steven Alan pocket tee was just the ticket in that regard — especially when paired with my Grayers Ivy Blazer, a casual linen-cotton jacket with unique patch-button pockets and a casual feel. If you’re looking for a way to dress down your summer blazer, you can’t go wrong with a garment-dyed tee. The combo helped me move in style around the trade show, as did a pair of sharp-yet-edgy Levi’s 505C Jeans, made with a hint of stretch and featuring a faded grey-black wash. They’re a slightly cooler take (figuratively and literally) on heavy dark denim and a blazer, particularly when moving around a lot. I finished off the combination with a pair of rugged Timberland leather chukka boots and my ever-dependable Timex x Todd Snyder Mod Watch, a frequent travel companion and just one of a few stunning watches from the Timex x Todd Snyder partnership.

With Day 1 in the books, it was a quick turnaround for another busy day at Sands Expo at The Venetian scoping out the bustling (and hustling) crowd of #menswear aficionados. Throughout the day, I checked out the wares on display from perennial Style Guide favorites like Red Wing Heritage and (potential) soon-to-be favorites like Hudson Shoes.  It was a great mix of brands, including everyone from accessories companies like Herschel Supply Co. to sock brands like Happy Socks. All the while, I again took on the day — and the heat — in style. I stuck with some of my favorite style essentials, like my JackThreads Denim Shirt (a very wearable shirt no matter the season). I complemented that with my Taylor Stitch Slim Stone Chinos — they’re unbeatable for the price and quality.  And when you’ve got versatile staples like those two pieces, stylish Steven Alan sunglasses and sturdy leather chukka boots are a nice finishing touch (the pair seen here is from Timberland — you can snag a similar style from Thursday Boots for a nice value).  On the accessories front, my ever-reliable Timex x Todd Snyder Mod Watch was the perfect timepiece for the occasion — it goes with just about everything thanks to the crisp retro dial and grey NATO strap. For being on time to various meetings and catching up with friends (all on the job), it helped keep me in line. That outfit combination worked well for the evening, too — it’s not every day you get the chance to attend a party thrown by the Hearst and Esquire teams (yes, that Esquire). Luckily, my smart-casual combination was able to take me from a day on the trade show floor to enjoying some delicious cocktails without missing a beat (that’s what we’re all about here at The Style Guide).

A comfortable, casual and crisp travel outfit. Polo by Life/After/Denim. Warren Denim by Mott & Bow. Chariot Runner Sneakers by Mott & Bow. Steno Book by Field Notes Brand. Waterbury Chrono by Timex x Red Wing Heritage. Slim Mailbag by Satchel & Page.

A comfortable, casual and crisp travel outfit. Polo by Life/After/Denim. Warren Denim by Mott & Bow. Chariot Runner Sneakers by Brooks Heritage. Waterbury Chrono by Timex x Red Wing Heritage. Steno Book by Field Notes Brand. Mailbag by Satchel & Page.

Sadly, my time at Liberty Fairs came to an end all too quickly — today called for a flight back to NYC. For one last push through the heat of Vegas, I grabbed the aptly named Marco Polo from Life/After/Denim. It blends a modern fit with a garment-washed look and feel, plus an open collar (one featuring no buttons). The overall effect is breezy and casual, but it’s one that still looks put-together for a cross-country flight when teamed with the ever-stylish Slim Warren Denim from Mott & Bow. For only about $20 more than what the brand normally charges, you’re getting a well-fitting pair of Italian-made denim — they were the perfect complement to my lightweight Brooks Heritage Chariot Runners in color and silhouette. Throughout the day, kept track of my flight time with my Timex x Red Wing Waterbury Chrono and chronicled my adventures with my handy Word Notebooks Adventure Log — both of which you should bring along for a weekend getaway.

As great of a time as it was in Las Vegas, it was even better to reconnect with great friends and fellow bloggers — plus, some terrific brands you’ll (hopefully) see a lot more of here and on my Instagram in the coming months. Forging partnerships and featuring great brands and products is terrific, but meeting great people in a like-minded environment is even better.  Even though it’s been a heck of a busy week so far — and it’s only Wednesday (!) — my travels aren’t quite done yet. We’re looking at one day back in NYC before I hit the road on Friday to head back to my hometown of Mason, Michigan for my great friend Andy’s wedding. Seeing my friends for his bachelor weekend in Grand Rapids was an absolute blast just a few weeks ago, so this upcoming trip is bound to be just as incredible (even if it’ll be powered by lots and lots of coffee). If you’ve got menswear musings or questions on what to wear for your next Las Vegas trip, shoot me a tweet on Twitter or follow along on the daily via Instagram.

Look for the Friday Read and Style Pick later this week, and swing back through the blog on Monday for yet another Michigan trip recap — stay stylish!

-Beau
Buck Mason - Timeless Design. Made in America.