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Most Comfortable Chukkas

Most Comfortable Chukkas

Almost as casual as all leather boots get, Chukka boots were first worn by British soldiers in Africa during WWII. The footgear later made its way across the Atlantic, becoming a casual staple in the 20th century. Today, chukka boots are gracing the feet of stylish men in colder months.

Chukka boots provide a great way to demonstrate your own special and sophisticated sense of style. Easy to dress up or down, Chukkas are a versatile footwear option that will serve as a reliable companion that you can count on.

In this article, we reviewed some of the best chukka boots available for purchase. They are all well-made, durable, and most importantly comfortable to wear for long working shifts.

Here are the Most Comfortable Chukkas

Red Wing Heritage Men’s Work Chukka 

Made in the USA with locally sourced leather, the unique look of the Red Wing Heritage Men’s Chukka is a hint of seamless quality. Initially designed for lightweight-duty labor, shoppers can rest assured that these chukkas are made to last and are great for work.

The leather insole delivers much-needed support for those who are on their feet all day. Though not the cheapest on our list, Red Wing Heritage Men’s Work Chukka will stand the test of time if you won’t mind paying more upfront. Moreover, these boots are resoleable and are offered in a selection of colors and sizes.

Bruno Marc Urban Suede

Perhaps the most important thing in every Chukka boot is comfortability. Fortunately, Bruno March Urban Suede is designed for much more than just comfort. The cushioned footbed means that your feet will always stay relaxed and comfy no matter how long the shift gets. Available in 15 colors, buyers can easily combine these with any pants or suit and still look classy.

Speaking of performance, you’ll hardly go wrong with these boots as they’re built to complement almost anything you wear. Plus, you don’t have to stress over looking awkward as they are incredibly versatile.

The material employed here is high-quality suede leather and a durable outsole. You’ll also find suede upper, three eyelets lace-up, and a non-skid outsole. The heel measures approximately one inch while the platform comes in at around 0.5 inches. For a sharper look and sophistication, the boots feature a contrast stitching on the vamp.

Sorel Men’s Madson II Chukka Boot

If you’re on the hunt for the best Chukka boot for winter, be sure to give the Sorel Men’s Madson II a try. These boots boast a rubber outsole that ensures a steady and confident grip with every step. Whether you’re running through the rain, probably to catch a cab, or are trudging through several inches of snow, you will never have to stress over the performance of these boots.

They are equipped with some waterproofing properties in both the full-grain leather and suede varieties. That means your feet will remain dry and comfortable throughout the day.

Nisolo Emilio Chukka Boot

Mending the gap between casual and formal footwear, the Nisolo Emilio chukka boot is sleek, minimalist-inspired footwear that’s ideal for numerous occasions. You can effortlessly dress these up or down because they are versatile too.

These chukka boots feature a nubuck leather upper, integrated with a full-length soft leather insole. Also, the thin laces on the front are streamlined to easily elevate the fashion level of this boot. On the bottom, the whole thing rests on a leather outsole that is combined with a rubber heel cap. This brings about the much-needed grip during the winter months.

The boots are available in half sizes ranging from 8-13.5, and they run true to size. On top of that, the Nisolo Emilio Chukka comes in a selection of colors.

Red Wing Heritage Weekender Chukka

Those looking for the best Chukka boots made in the USA are bound to be impressed by Red Wing Heritage Weekender Chukka. No doubt that you’ll smoothly transition from work to the weekend style with these boots.

Developed with all the classical approaches that have kept Red Wing at the forefront of men’s footwear, the Weekender Chukka is versatile, easy-going, and comfortable. The boot is made with premium waterproof leather, so you don’t need to worry about elements. Still, if you’re a self-proclaimed king of the outdoors, then look no further as these sturdy boots are exactly what you’re missing.

CLARKS Men’s Bushacre 2 Boot

The same guys who made the Original desert boot, Clarks, are now offering a tad more of a casual and budget option with their Bushacre 2 Chukka boot. It’s one of most people’s favorite chukka boots, thanks to the timeless and agreeable price point (about $60). Though the leather quality could be improved as it’s made from genuine leather. The Bushacre 2 is still capable of lasting you a season or two before calling for a replacement.

If you’re searching for the perfect chukka boots, something that will go with nearly anything you want, search no more. The shaft measures around 4.5 inches from the arch while the platform comes in at 0.25 inches. The heel is one inch.

Allen Edmonds Williamsburg Chukka Boots

Where cost isn’t a concern, and you’re interested only in the very best, then be sure to consider the Allen Edmonds Williamsburg Chukka Boots. Handcrafted in Wisconsin, employing premium calfskin leather, these boots have no flaws as far as construction is concerned.

Aside from feeling soft and velvet-like to the touch, the leather also looks and gets better with time as the patina develops. The resoleable welt means you can bring them to your local cobbler for a refresh when the time is right.

Thursday Boot Company Scout Chukka

The Thursday Boot Company is one of the best water-resistant Chukka Boots on the market. Indeed, they’re the modern take on the famous British desert boot. The boot is refined with a complete American Flare that’s both classic and contemporary.

Derived from premium suede, a repairable Goodyear Welt construction, and studded soles, the boot is truly sturdy. The brand does details right, these chukkas are lined with buttery-soft glove leather and augmented with weathersafe Hydrophobic Coating. Irrespective of where life takes you, these boots promise to help keep up with the best of them.

Astorflex Greenflex Dress Chukka

Handcrafted in Italy, this leather Chukka boot by Astorflex balances between form and function. The high-quality leather looks beautiful and will comfortably last you seasons. On the bottom of the Chukka is a 100% natural crepe rubber sole. This squishy outsole delivers an excellent balance of both comfort and grip.

The leather uppers look soft, meaning the boots are well-suited for smart casual wear. The Astorflex Greenflex Dress Chukka is available in a variety of sizes, from 7-15, and in three distinctive colors: tan, nubuck, and dark brown nubuck. You won’t have any problem finding the right boot that meets your unique tastes.

Brooks Brothers Chukka Boots

The Brooks Brothers Chukka Boots are among the most stylish options on the list. The quality and craftsmanship are quite above the boots’ $200 price point. The boots provide an awesome balance between high quality and affordability. They are carefully crafted from fine materials and unparallel welt construction so you won’t be having problems wearing them. Moreover, the high-density sole is meant to provide great support during performances. The boots are versatile and are available in eye-catching colors.

How to Wear Chukka Boots

Initially made from unlined suede leather on a thin outsole, Chukka boots are currently available in a range of different materials and colors. Whatever you choose, Chukka is a style of boot that sits comfortably in modern wardrobes. They are versatile enough for use in the office as well as the pub.

Chukka boots are among the best boots to wear with jeans, though you can always play on the style’s upper-class heritage. They are known to be a smart-casual crossover, but that can be attributed to the leather. For instance, a light suede can lend a very different feel from a highly polished version. They tend to look great with a narrow trouser leg, either kinked on the shoe or probably an inch or so above the boot.

Chukka boots are often found in shades of brown, but you can always find a variety of colors in the market. These boots look similarly great with jeans or chinos and more formal outfits. Meanwhile, if you want to style them up, opt for darker hues and keep off from contrast color soles. Black suede chukka boots look good with simple flat-fronted pants, a button-up shirt, and a little flash of socks. For more casual, regular wear, you might want to go with some selvage denim or a pair of Dockers Alpha.  Or even a crew sweatshirt.