The Tuesday Steal: These Astorflex Chukka Boots are the Perfect Fall Chukka Boots Right Now

Welcome to another quick-hitting edition of The Tuesday Steal, where today, we’re all about the best chukka boots for men to lace up as we head into early fall. Heck, this won’t be the last post on the blog this week about the best men’s boots in general (or on the best new menswear for fall), so you’d better get used to it. And yet, I’d wager the well-crafted, sustainable Astorflex Ettoflex Boots are going to be a mighty easy pair of boots to get used to wearing as we draw ever closer to Labor Day and early fall. As sold by Huckberry, they’re about everything you could ask for in a pair of the best transitional boots: Neither too lightweight nor too bulky, neither too flashy or too boring. That qualifies them handily as some of my new favorite chukka boots, and you very well might feel the same way.

If you’ve had the chance to try any Astorflex chukka boots, you’re in luck as far as that same quality and attention to detail is concerned. For starters, any and all Astorflex chukka boots are made sustainably, a huge bonus as far as fashion and function is concerned. The use of European leather only gets more impressive when you consider that it’s aged naturally for 30 days in a combination of water, bark, oak and powdered mimosa. The result is a supple and stylish leather that really lends itself quite well to a pair of the best chukka boots for men.

SHOP: The Astorflex Ettoflex Boots

The Astorflex Ettoflex Boots are also a bit more sporty than a classic pair of Astorflex chukka boots, although there’s nothing wrong with having more than one pair in your rotation. It’s the crepe wedge outsole that gives this pair of chukka boots a blend of durability, style and rugged appeal (never a bad thing to have in your footwear rotation). The roughout leather used on the Astorflex Ettoflex Boots is also tough and uniquely textured, a fitting fall style move when worn alongside, say, some Flint and Tinder jeans for a breezy late summer or early fall day.

The memory foam insole is also lined in calfskin for plenty of comfort through long fall days strolling through the park or visiting a favorite brewery. The Astorflex Ettoflex Boots are also polished enough to wear to the office in business casual situations, though. A rugged shawl cardigan and the expertly cut Flint and Tinder 365 Pants are a fine match for the well-made, versatile and exceedingly comfortable Astorflex Ettoflex Boots. What are you waiting for? If you do end up trying them out, be sure to let me know on Twitter. Here’s to the start of fall, folks!

SHOP: The Astorflex Ettoflex Boots

#OOTD: How to Wear the Best Men’s Chukka Boots This Summer

If I’ve said it before, I’ve said it a million times. The summer heat is no reason to relegate your chukka boots to storage. Why, just last month here on the blog, we talked about the best leather chukka boots you can buy for spring, the sort of pair that blends proper durability with style points and handmade craftsmanship. Those chukka boots, in fact, are back in a big way today as we explore yet another #OOTD, this one focused on, well the best way to wear chukka boots for summer. The key is keeping it light, breezy and casual-yet-cool, because the best chukka boots for men are the kind you can wear with mostly anything in your wardrobe, and just about anywhere (even to the office, once you check out the iconic dress watch in this ensemble). It helps that today’s featured chukka boots come from Veldskoen, which has a storied history of making chukka boots for hot weather.

When you don’t quite want to lace up canvas sneakers and it’s also far too hot for sturdy leather work boots, chukka boots are a great go-between. Especially if you’re spending time around and heading somewhere that requires a bit of polish and style (patio cocktails, anyone?), the best men’s chukka boots are just what the (style) doctor ordered. The supporting cast is packed with summer style essentials, including a stylish short-sleeve shirt from Huckberry. Tread carefully, select the best boots for summer and relish in the fact that you’ll have these Veldskoen chukka boots far past this season. Happy shopping, my friends.

The best way to wear chukka boots this summer

  • The Chukka Boots: Veldskoen Leather Chukka Boots, $179 — When the time comes to reach for dependable summer shoes, consider rugged-yet-lightweight, classic men’s chukka boots.
  • The Shirt: Wellen Hemp-Cotton Button Down, $68 — Keep things nice and breezy up top with this sustainable hemp-blend shirt from Huckberry.
  • The Lightweight Pants: Marine Layer Saturday Pants, $125¬†— These stylish drawstring pants look like chinos on the surface, but wear like comfortable sweatpants. Perfect for breezy summer days aplenty, and they’re possibly the best pants to wear with chukka boots.
  • The Socks: Mack Weldon AIRKNITx Ankle Socks, $18¬†— Get that “no socks” look without resorting to going barefoot. These comfortable ankle socks are the right accessory to keep you on your feet with functionality in mind. Oh, and¬†Mack Weldon offers free shipping, too.
  • The Grooming Essential: Triumph & Disaster Coltrane Clay, $30 via UNCRATE¬†— Shape your fresh, post-quar haircut with one of the best hair clays for men, folks.
  • The Watch: Shinola Runwell Leather Watch, $1,095¬†— Here’s the kind of stylish leather dress watch you can wear to the office and then to happy hour, or else to a cool-as-can-be summer party on the weekend, without missing a beat. The Shinola Runwell never fails, easy as that.¬†
  • The Sunglasses: Pacifico Optical Buckler Sunglasses, $195¬†— A sleek and on-trend #OOTD like this requires some of the coolest men’s sunglasses, like these round-frame shades in a crisp colorway.
  • The Everyday Carry: Mission Workshop 500D Drift Tote, $235¬†— Perhaps you’re not quite in need of a rugged tote bag like this one, but if you’re going to be out and about all day, it pays to pick up this much-loved Mission Workshop tote.

Does this #OOTD have you looking ahead to warmer days without much on your agenda besides getting another ice-cold beer at your favorite bar? Wherever you go — even if you decide to wear your new favorite chukka boots to the office — I’d say it’s well-suited to any style demand you can dream up. Start out with classic men’s chukka boots to set the tone (more casual than dress shoes, more polished than sneakers). Keep it breezy from there with a sustainable button down shirt from Huckberry, then throw on the best pants to wear with chukka boots to really drive home this effortlessly cool look.

Keep the details on point, too: A pair of comfortable ankle socks are a surprisingly underrated move when wearing chukka boots and straight leg pants (roll ’em up just a bit to show off some ankle). Shape your hair accordingly with one of the best hair clays for men, a nice way to put a bit of extra effort into this #OOTD. No matter where you go, a stylish leather dress watch is going to polish things up quite nicely with sharp looks, too. Elsewhere on the accessories front, some of the coolest men’s sunglasses will top this look off handily. And to haul your EDC picks, you know what to do: Grab the Mission Workshop tote and load it up at well. For expert, laidback-yet-cool summer style, you’ve just found the best men’s style essentials. Cheers, folks!

The Thursday Buy: These Classic Leather Chukka Boots from Veldskoen Are a Spring Must-Have

Veldskoen men's boots

Some of the coolest chukka boots for men you can step into right now.

You don’t need me to tell you that having the best shoes for spring on your feet is a necessity, right? Long gone are the days of lacing up your winter snow boots or clunky work boots — opt for some of the best chukka boots instead, as you welcome the slow-but-sure return of sunshine, breezy days, outdoor patio beers and more. Are we on the same page today? Good, great, grand. And in today’s Thursday Buy, do I have just the pick for you: The Veldskoen Chukka Boots are well-made, affordably priced, expertly crafted and ideal for spring days and nights.¬†Just as you need a pair of casual retro sneakers for spring and summer days aplenty, the right pair of classic leather chukka boots for men can indeed go a very long way.

Frontier 40

Think of the Veldskoen Chukka Boots as an alternative boot option to Clarks, a nice change of pace if you want something new (yet made with heritage quality in mind). And if you’re not familiar with South Africa’s Veldskoen, now is the perfect time to get acquainted.¬† Veldskoen makes its boots using old-school methods and ethical materials, to go along with sustainable sourcing and a close means of production with workers who are paid a fair wage. They’re hand-cut and handsewn, and the end result (especially when it comes to the understated, practical and stylish Veldskoen Chukka Boots) is nothing less than your new favorite pair of spring boots.

SHOP: The Veldskoen Chukka Boots

Veldskoen chukka boots review

Durable, classic, cool and sustainable — that’s Veldskoen for you.

You could make the case that every guy needs a pair of the best leather chukka boots, especially a pair that’s more comfortable to wear than your standard leather lace-up boots and somewhat dressier than your go-to canvas sneakers. The Veldskoen Chukka Boots toe that line quite nicely, literally, and the fact that they’re durable and won’t give out on you after a few wears is a major bonus (to say the least!).

The recyclable rubber compound sole gives you both cushioning and all-day comfort, and the memory foam insole is designed to mold to your foot over time (my own pair is certainly doing this after wearing ’em this season). They’re timeless and understated, ready to be worn with your favorite pair of tan chinos and a rugged henley — you can find both at the Shop By The Style Guide — or else with easygoing light wash jeans and a classic pocket T-shirt. With Veldskoen Chukka Boots, the styling potential is endless, and the timeless looks are nearly guaranteed. Happy spring, my friends.

SHOP: The Veldskoen Chukka Boots

See Now, Buy Now: These Taylor Stitch Chukka Boots are Classic Boots for Spring

Stepping out in style this spring with rugged chukka boots from a classic brand.

If you’re anything like me, perhaps you’ve got quite the affinity for gear from San Francisco-based Taylor Stitch — from the brand’s rugged denim jackets to stellar shirting, these gear purveyors have been a longtime favorite of yours truly (going back to the early days of the blog, in fact!). And now, they’ve done it again with some of the best chukka boots for spring — heck, some of the best chukka boots on the market, period. As we work to transition our wardrobes slowly but surely toward warmer weather, classic leather chukka boots are as reliable a footwear option as it gets. Maybe you won’t need them right¬† now during these wild times of COVID-19 (yes, sorry, I went there!), but you will soon enough. Rest assured, you’ll hear plenty more about this style in the weeks and months to come, but for now, let’s talk about the Taylor Stitch Chukka Boots in Tumbled Sedona — again, folks, these are your new favorite chukka boots … easily. With a lighter weight than your tough snow boots, and a bit more polish than your favorite sneakers, there’s no question that these Taylor Stitch chukka boots (made from positively beautiful, supple 4oz. Sedona leather) check all the right boxes in matters of style and functionality.

SHOP: The Taylor Stitch Chukka Boots in Tumbled Sedona

The difference is in the details with these Taylor Stitch boots, per usual — and that’s a great thing indeed.

What’s more, some of the best men’s chukka boots will have serious staying power starting right now in early spring, then carrying over into summer & back to fall. Truly, you can rock these rugged chukka boots with the basics (I.E. A classic Taylor Stitch chambray shirt & slim chinos) and with more luxurious items (a breezy khaki cotton suit, for starters). And if you feel like keeping things casual & rocking these with a cotton pocket tee and faded blue denim? That’s a style move you should certainly make, no questions asked. The Vibram sole and Goodyear welt construction provide that crucial blend of durability and comfort — there might be a brief break-in period, based on my past experiences with Taylor Stitch boots, but once you’ve started wearing these classic chukka boots, you’ll find it tough to stop. And as with other Taylor Stitch menswear, you’ll assuredly find they get better the more you wear them. Don’t waste another second — shop these right now.

SHOP: The Taylor Stitch Chukka Boots in Tumbled Sedona


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


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? 

Style Pick of the Week: Hudson Shoes Lewiston Chukka

Hudson Shoes

The handsome pair of chukka boots to get you ready for fall.

Alright, Style Guide readers. I’ve got good news and … more good news. The good news is that you’re really going to like today’s Style Pick of the Week. The better news is that we’re one week closer to everyone’s favorite #menswear season — fall. OK, maybe jumping the gun a bit (or a lot). And yet, it pays to be prepared when it comes to the best men’s gear for the season — right? So, let me introduce you to the Hudson Shoes Lewiston Chukka. Yes indeed, the Lewiston Chukka is a heck of a pair of chukka boots to put on your shopping list for fall. Heck, they can help you step into any situation in style, at any point in the year. Seriously. A classic pair of men’s chukka boots can work wonders with the simplest outfits. A stylish Oxford shirt and slim dark denim? Throw on leather chukka boots. Slim grey denim, a henley and a blue denim jacket? Lace up the Hudson Shoes Lewiston Chukka. A herringbone blazer and navy chinos when the fall rolls around? The Lewiston Chukka is your best bet. And the best part is, you can get ’em for a nice deal through Bespoke Post. The cognac leather upper is all style, while the leather lining is all comfort. And the rubber sole is made for navigating tougher terrain than your average pair of dress shoes. That’s really not all the Lewiston Chukka offers, truly.

Hudson Shoes

A closer look at the sleek profile of the Hudson Shoes Lewiston Chukka.

In addition to the solid price for a pair of year-round chukka boots, you’re getting neat design by way of Britain. Like the Crockett & Jones chukka boots that James Bond wears so well in “Skyfall,” the rubber sole on the Lewiston Chukka adds a bit of durability and traction in the rain and on other slippery fall surfaces. Again, just because it’s August doesn’t mean you shouldn’t look ahead. To wit: The Lewiston Chukka is going to sit just right under grey flannel trousers and a navy topcoat on a blustery day, and you can even wear ’em to the office and then to happy hour after without needing to switch them out. ¬†That’s what I’m talking about, folks. All of that means you should give the Lewiston Chukka a serious shot now –and later in the fall season. Oh, and the custom stitching means you’re getting something no other shoe brand can bring to the table; well-done, Hudson Shoes. So, what do we think of the Hudson Shoes Lewiston Chukka? Are we ready for fall? Rest assured, we’ll be talking more in the months to come about the best men’s boots for fall and beyond — and you can expect the Lewiston Chukka to make that list.

Hey — stay stylish!


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

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.

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?

Shop the latest in Men's styles Under $50 + get FREE Shipping on orders over $100 at Frank & Oak!