Top 20 Best Chukka Boots For Men

Top 20 Best Chukka Boots For Men – A Stylish Step Forward

To highlight Midwestern aesthetics alongside outdoorsy ambitions, all a guy needs in his wardrobe is a dynamite pair of chukka boots. This kind of footwear demarcates the epitome of 21st century desert chic.

No man’s closet is complete without the distinct grandeur of chukka boots.

These magnificent boots are an indispensable part of masculine living. Their shrewd appeal stems from universal adaptability. These suave contraptions are idea for lengthy walks in the wilderness, but they can also make a striking first impression at your next business conference. When a fellow has the right set of chukka boots, the actual occasion is irrelevant. His stylish demeanor will be unabashedly defined from the get-go.

These rugged boots are typically built to endure strenuous terrains and environments. Many of them are waterproof, and all of them provide ample support for the feet. An increased sturdiness is accompanied by improved posture and a boosted height.

Of course, it is wise to spend time perusing different brands before committing to an expensive pair. These shoes are available from a variety of distinguished manufacturers, so don’t hesitate to weigh your options. In fact, we’ve compiled a complete list of today’s most renowned chukka creations. After you explore the astonishingly wide-ranging possibilities, it will be hard to narrow your final selection down to just one.

Luckily, you don’t have to stick with a single set; remember, many of these top 20 best chukka boots for men are much more affordable then they look. However, that doesn’t mean that there aren’t gallantly expensive varieties too.

Best Chukka Boots For Men

1. Timberland Ek Brook Park

Timberland Men's EK Brook Park Chukka Boot,Black Smooth,14 W US


Timberland’s latest Brook Park leather men’s chukka boots arrive with a clean low cut design and sharp lines. Each features a rock-solid construction that’s finished in premium full-grain leather. At the bottom of every boot you’ll find Timberland’s unique L7 traction lug outsole for stellar performance and wear resistance. To keep your toes comfy, there’s also geometric cone support for reducing shock and taxing long days spent on the feet.

For the finishing touches, the Brook Park arrives with 100% organic cotton laces and a red/navy striped pull tab on the rear of the heel. To match your attire, you’ll be glad to know there are seven different color variations to choose from, including two non-leather suede options.


2. Calvin Klein Ulysses Suede

Calvin Klein Men's Ulysses Suede Boot,Dark Brown,11.5 M US


Stepping into style is easy with the deep, rich suede found on Calvin Klein’s latest Ulysses men’s chukka boots. Regardless if you go with dark navy, dark brown, charcoal or black, each features a finish far from flat. You’ll find a sharp looking strap on the rear too for a bit of eye catching appeal and added functionality.

In terms of comfort these chukka boots feel as great to walk in as they do to look at. From casual weekend nights out on the town to more professional days the office, the suede exterior blends well into just about any occasion.


3. Clarks Originals Desert

Clarks Originals Men's Desert Boot,Beeswax,10 M US


For the gentleman who’s ultra-picky about finding the perfect look, you’re in luck! When it comes to the Clarks Originals Men’s Desert Boot you’ll be glad to know they come in 73 different variations with leather and suede exteriors. Each arrives with an inspiration taken from the traditional crepe-soled boots once worn back in WWII by British officers.

However, these men’s chukka boots are more than just attractive eye-candy. The moment you put them on you’ll know the real reason as to why their extremely popular among concerning gentlemen. After breaking them in, the genuine plantation crepe outsole paired with a leather covered EVA footbed makes walking around feel like you’re doing so on a cloud of comfort.


4. Kenneth Cole Reaction Desert Canyon

Kenneth Cole REACTION Men's Desert Sun SU Chukka Boot, Black Pebbled Leather, 11 M US


Kenneth Cole Reaction’s men’s Desert Canyon chukka boots look as comfortable as they feel. While sizes might run larger than most, each is a breeze to step in thanks to a finely padded footbed. On the exterior you’ll find two classy leather finishes including brown and black.


5. Clarks Bushacre 2 Desert

Clarks Men's Bushacre 2 Chukka Boot,Dark Brown,8 M US


When it comes to popular men’s chukka boosts the Clark’s Bushacre 2 Desert ranks among the cream of the crop. Aside from 18 impressive color choices in leather and suede version, each features a solid construction and streamlined exterior design. Of course, a synthetic crepe sole keeps your feet extremely comfy while being less springy and more durable than the original Desert Boot.

Keep in mind, sizes run slightly larger than you’d expect.


6. Cole Haan Glenn

Cole Haan Men's Glenn Chukka Boot,Java,8.5 M US


These three-eye chukka boots from Cole Haan arrive with a distressed suede exterior and tonal laces. To top off the look on the Glen Chukka Boot, Cole Haan also added really nice contrasting stitching in addition to a fine multi-stained wood stacked sole.

Best of all, they pair flawlessly with a fine pair of jeans and even work a considerable amount of stylish magic in more professional environments.


7. Cole Haan Grover

Cole Haan Men's Grover Chukka, Denim, 9 M US


Meet the fashionably well-crafted Grover Chukka Boots by Cole Haan. Each lightweight two-eyed chukka boot arrives with welted stitching and a stacked heel in a beautiful wood design. For style options, you’ll be glad to know Cole Haan offers the Grover in five different varieties.

There’s the classic take with black and chestnut leather, plus steel grey and milkshake suede. Of course, there’s also a really sharp denim version as well.


8. Steve Madden Harken

Steve Madden Men's Harken Chukka Boot, Cognac, 10.5 M US


One look at these Steve Madden Harken men’s chukka boots and you’ll be surprised by the price tag. It’s lower than you’d think even with the gorgeous leather exterior and classy design. In terms of value you certainly get a lot of it in addition to compliments of course.

Now, aside from being perfect for more dressy to casual occasions, the only real downside comes during the break-in process. The Harken chukka boots tend to be harder, or better said, tougher to wear down at first. For a bolder look with a little more flair to the same design, the Hestonn Boot by Steve Madden is worth looking into.


9. Stacy Adams Cagney

Stacy Adams Men's Cagney Chukka Boot,Black,11 M US


The Cagney Chukka Boot by Stacy Adams arrives with sleek, supple leather exterior for a well-polished look. To make life easy on your toes you’ll find a Suedetec lining for superior breath-ability alongside excellent cushioning comfort. For keeping your foot grounded, there’s also a flexible rubber sole with a fine triangle pattern to provide plenty of traction.


10. Ferro Aldo Ankle High Desert Lace Up Dress Chukka Boots

Ferro Aldo Men's 806380E Ankle High Desert Lace Up Casual Dress Boots, Black, 12


Ferro Aldo’s ankle high desert lace up chukka boots mix a bold impression with a sophisticated presence. Sure, they cost significantly less than most, however that doesn’t mean they lack any substance or style. In terms of value, you can acquire the designer look without the designer price tag attached to it.

To perfectly match your attire, you’ll find three different color versions available including wine, brown and black. All of which come paired to a beautiful wood outsole and brown leather lace trim on top.


11. Rockport Harson Lace Up

Rockport Men's Charson Lace-Up Boot-Black-10.5 M


Rockport’s Charson men’s lace up chukka boots mix rugged with professional. With eight options to choose from including leather and suede, each arrives with full-welt stitching and a durable lug outsole. Just keep in mind to go with a size larger, as they tend to run about half a size too big.

In terms of look and feel, the leather texture is rich and wears into a beautiful patina over time. While comfort is unbelievably faultless thanks to a soft fabric lining and Adiprene shocking absorbing heel originally designed by Adidas.


12. Kenneth Cole Unlisted Real Estate

Kenneth Cole Unlisted Men's Real Estate Chukka Boat, Grey, 8 M US


While the suede stands out fashionably, you should know they are quite snug at first. In other words, these Unlisted Real Estate Chukka Boots takes some time getting used to. Given their charming good lucks, that probably won’t be a problem since you’ll want to wear them literally everywhere. They pair great with everything from jeans to dress pants, plus with three different colors available it’s easy to expand your wardrobe choices.

Kenneth Cole offers this chukka boot in three sharp colors including grey, taupe and navy. No matter which you go with, you’ll find great contrasting details on all of them like cream laces, and a striped red rubber outsole.


13. Ted Baker Torsdi2

Ted Baker Men's Torsdi 4 Chukka Boot, Tan, 10 M US


Ted Baker’s Torsdi2’s feature a minimalist design, yet, they manage to make such a striking impression. The beautiful exterior leather is quite breathtaking against the fine contrasting color stitching detail and wooden outsoles. All put together, these men’s chukka boots are classy enough to go from work days to weekends in an exceptionally fashionable and fitting manner.


14. Deer Stags Seattle

Deer Stags Men's Seattle Boot,Black,10.5 M US


A stylish look for the modern man, meet the Deer Stags Seattle men’s chukka boot. Each arrives with a traditional lace-up closure, elegant rubber outsole with wood touches, and a smooth, supple leather upper exterior. You’ll find the decorative stitching subtle yet, eye-catchingly well crafted.

On the inside you’ll find a super soft lining and removable foot bed for all day long comfort.


15. Cole Haan Colton

Cole Haan Colton Chukka Boots For Men

After buying my first pair of Cole Haan’s Colton Chukka Boots, I ended up buying a second. I’ll probably own a third pair after that if they keep making them. When it comes to the copper and peacoat leather exterior it’s not only stunning to look at but extremely durable. Paired with a sharp wood outer sole and a rubber coated heel sole, you’ll find great contrasting style going on too.

Through three winters with grounds paved in rock salt and thick snow to rebuilding a wood deck in the mud, and much more, these boots just won’t quit on me. Though, I have gone through seven pairs of shoe laces to put thing in perspective. Now, while I don’t like picking favorites, if there was a chukka boot that at top of my list it would have to be the Colton.

Unfortunately, their significantly pricier than most at over two-hundred dollars a pair. However, they showcase plenty of truth in the statement, you get what you pay for.


16. Clarks Newkirk Top

Discover a different take on the classic men’s chukka boot with sharp modern lines. The Clarks men’s Newkirk Top Chukka Boots arrive with a mix between casual and professional. Available in two different leather stains including dark brown nubuck and black, each is paired with a stacked midsole and sleek contrasting stitches.


17. Sebago Halyard

For a more casual but fun men’s chukka boot the Halyard delivers flawlessly. Sebago really paid attention to the fine details by opting to add a sharp debossed logo and contrasting leather patch above the woodgrain heel. In terms of colors, there are four to choose from including dark khaki, brown nubuck, grey nubuck and black suede. Regardless of which you choose you’ll enjoy comfort right out of the box.


18. Ted Baker Pericop

The Ted Baker Pericop Men’s Chukka Boots are about as classy and professional it gets. Each lace up boot arrives with a stunning attention to detail which lends itself to any dressy occasion. A fine leather exterior is eye catching while beautiful broguing ties everything fashionably together. To elevate the already handsome appeal even higher, Ted Baker has also added contrasted stitching and a remarkably elegant wood stacked sole.


19. Sebago Tremont

Sebago’s Men’s Tremont Boot arrives in four stylish options, all of which, feature a sharp leather exterior. Each chukka boot has a single-stitched welt, three blind eyelets and a wood stacked heel. Now, aside from the great color choices like mahogany, black, dark brown and brown, there is one more thing to consider. When it comes to sizing on the Tremont Boot it runs larger than most; make sure you go with a smaller size for a snug fit.


20. Steve Madden Saxxen

Steve Madden Men's Saxxen, Navy Suede, 13 M US


Stylish suede encompasses the exterior of Steve Madden’s fun, yet, fashionable men’s Saxxen Chuccka Boots. Each arrives with mixed-media materials for an interesting sense of character and unique appeal. You’ll find a wood-tone inset on the heel for a bold impression, and contrast stitching throughout the boot for a bit of pop.

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