huckberry 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.

Pair up lightweight chukka boots with a crisp pair of dark denim for a casual and patriotic weekend combo.

With it being the Fourth of July and all, we’re very much in a patriotic spirit here at The Style Guide. That carries right on over to footwear, and today’s made-in-America Style Pick, the Red Wing Heritage Weekender Chukka. Great footwear has been a focus as of late on the Style Pick series, including stylish leather sneakers fit for summer. But given that lots of us are hitting the road this weekend, there are certain things that should be in your bag and on your feet when it comes to what to wear for the Fourth of July. Crucially, a crisp, durable pair of chukka boots is a great way to upgrade your travel style. Seriously, a pair of chukka boots works with light wash denim casually, and fits right in alongside tan chinos for a more monochromatic, tailored look. The Heritage Weekender Chukka has just about everything you need for the weekend, too — note that sizes are somewhat limited (size 9-13), but as the boots run a half-size large, you might be all set to shop. Onto the specs — the Weekender Chukka is crafted from roughout leather that’s water, stain and perspiration-resistant, so it can tackle any hiking or walking across the weekend in style. Plus, the quality is self-evident, as it’s produced using S.B. Foot Tanning Company leather (just as the brand has done for decades on end). Still not sold on wearing boots in the summer? Bear with me — or walk with me?

A relatively trim silhouette, casual roughout leather and classic Red Wing styling touches make these worth the investment.

The Weekender Chukka takes a more casual, nuanced and lightweight approach to the silhouette, so it won’t weigh you down as much as a heavier pair of rugged winter boots. The Hill outsole is flexible yet dependable and durable, and the eye-catching striped yellow laces are a nod to classic Red Wing style. The brand’s ComfortForce footbed should also add to their wearability — an extra bit of reinforcement is critical when standing around waiting for fireworks or grilling out. Plus, the contrast stitching provides another point of visual interest, making them an even more casual pair of chukka boots. These are definitely chukkas you can rock with slim navy or olive chinos and a heather grey pocket T-shirt this weekend and beyond. And they’ll do just as well when worn with a slim short-sleeve henley and light chinos in a high-low style combo during other summer excursions. As to the rest of your style picks this weekend? Grab a durable weekender bag and maybe some other essential Fourth of July gear, and you’ll be set.

Get your pair of the Red Wing Heritage Weekender Chukka now (hurry!).

Enjoy the weekend, and go forth in style!

-Beau

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Tag / huckberry chukka boots

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

Style Pick of the Week: Red Wing Heritage Weekender Chukka