best guys’ chukka boots | The Style Guide

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.

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.

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?

#3. Johnston & Murphy Copeland Chukka — $155

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.

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

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.

#5. Red Wing Heritage Weekender Chukka — $230

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

Editor’s note: Expect these posts weekly detailing one standout item coveted by yours truly. Sometimes, these fit within budgetary restrictions and other times, they’re expensive splurges worth saving for. For more Wish List items from Beau, head here, and to see other Style Picks, head here.

One option to style the versatile Chocolate Suede Scout Chukka from Thursday Boot Company. Slim denim by Mott & Bow. Baseball jacket by Grayers. Burgundy henley by Pistol Lake. VIntage ballcap by Goorin Brothers. Leather gloves by Iron & Resin.

As my personal style has evolved over the years, my interest in footwear has grown, too. After all, learning more and more about clothes necessitates changing up how you dress for various occasions (from a job interview to heading to class and then work), and footwear goes hand-in-hand with that shift in perception. Now, I love my white sneakers for spring and summer, and I’m all about a sturdy pair of leather boots for fall and winter, but to me, there’s one type of shoe you can rock nearly year-round — the ever-reliable chukka boot. I’ve rocked the two-eye ankle boot style in some form for the better part of three or four years. Some are crafted from fine leather, some are crafted from suede; make no mistake about it though, the style fits in exceptionally well with everything from a polo and chinos in hot temps (ask James Bond) to a henley and dark denim in the chilly fall, as you can see here. And for the price, there might not be a better option than the Chocolate Suede Scout Chukka on the market right now from Thursday Boot Company. The brand has taken some flack from some online commenters out there (what footwear company hasn’t?) but my experiences have been nothing but great, and these chukka boots fit that bill as well.

Pair these boots with everything from slim denim to chinos (don't forget a pop of color in your sock game). Baseball jacket by Grayers. Stainless steel dive watch by Invicta. Slim denim by Mott & Bow.

A closer look at the pleasantly rich suede, which has held up quite well for the price. Baseball jacket by Grayers. Stainless steel dive watch by Invicta. Slim denim by Mott & Bow.

Crafted with a Goodyear welt construction that feels more sturdy than the price would suggest, the Chocolate Suede Scout Chukka in particular is an ideal piece of three or four-season footwear — think a tee and slim grey chinos in spring and a shawl cardigan and grey denim later in the year. And the dark chocolate color ensures they’ll do well in the transitional time of spring through the fall. Planning for lots of wear is even easier given that the suede is of great quality for the price — it’s smooth and sleek, and it’s held up well through a weekend exploring Washington, D.C. on foot. The full-glove leather lining is also quite soft, and one of the first things you notice about these boots is a slightly higher-cut ankle than your average chukka boot — that also extends the sleek feel and makes it easier to pair with slim denim. If you’re heavily invested in your footwear and used to paying substantially more than the purchase price of these chukkas, the Suede Scout might not satisfy you; if on the other hand though, you’re willing to pay a more-than-reasonable price for a versatile pair of chukka boots from a company on the rise, you’re in luck — Thursday Boots has you covered.

Editor’s note: Look for a full review of these boots in the weeks ahead.

Have you tested out any footwear from the brand? What’s your take on these chukkas and how would you style them?

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Tag / best guys’ chukka boots

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

Style Pick of the Week: Thursday Boot Company Chocolate Suede Scout Chukka