The Best Men’s Chukka & Desert Boots For Sharp Style & Strong Value

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Overall Best Chukkas for Everyday Wear ↓

Beckett Simonon Laval Chukka

Notable Features:

• Colors Available: 5
• Italian, full-grain leather upper
• Versatile and classic toe box
• Also available in Pull-Up Leather

Why We Like It:

There are two different styles of Beckett Simonon chukkas on this list, but their Laval model is our top choice for everyday wear because it’s an impressively elevated take on traditional chukka boots.

Beckett Simonon became one of my favorite brands after I reviewed their dress shoes a few years back, because they actually use the direct-to-consumer business model effectively.

By cutting out the middleman (i.e. the department stores that mark up and sell shoes at inflated prices), they’re able to combine luxury-quality craftsmanship with a reasonable price tag.

But while some DTC brands just mark the price up themselves and pocket the profits, Beckett actually passes the savings on to their customer, resulting in higher quality construction and materials than you usually get in this price range.

And the Laval is a great example.

Aesthetically, it’s a stunner, with richly colored calfskin leather and a toe shape that’s rounded but not too round.

It’s the perfect boot to wear to the office because it’s stylish enough to pair with business casual wear, but will look just as good if you head to the bar for happy hour after work.

In addition to the classic silhouette, it’s also well made, with an upper made from premium leather sourced from a gold-rated tannery in Northern Italy, and Blake stitched to the insole and outsole.

This is the type of chukka boot you can buy once and wear for a damn long time because it’s well-made enough to hold up for the long haul, and has the kind of timeless look that never goes out of style.

Why Some Might Not:

Some boot enthusiasts believe that the Blake stitch is inferior to Goodyear welt construction, so if you’re a Goodyear purist, this one probably isn’t for you.

This is also a versatile boot that can be dressed up or down, which I tend to think of as an advantage, but some guys might count as a negative.

If you’re specifically looking for the type of rugged boot that you can wear on a job site, or (on the other end of the sartorial spectrum) a sleek pair of chukkas that you could wear with a suit, I suggest you keep scrolling.

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Most Comfortable Chukka Boots for Men ↓

Nisolo Everyday Chukka

Notable Features:

• Colors Available: 4
• 5-layer memory foam insole
• Waterproof leather upper
• Gripped rubber sole

Why We Like It:

Formerly known as the Emilio chukka boot, Nisolo’s Everyday chukkas are comfortable boots that also happen to look f*cking fantastic.

On the comfort front, they include an insole made from five-layer memory foam, which moulds to your feet over time and provides built-in arch support.

On the style front, the rounded toe shape gives them a timeless casual look, and the heel cap is a nice touch that makes them look a little more like a classic chukka boot.

My favorite thing about these boots is the thin leather soles, which are sleeker than you’d expect to find on a casual, waterproof boot like this.

But even though they’ve got thin soles, they also have a grippy rubber heel cap that provides traction when the ground is slick, which is a nice example of a single feature providing both style and practicality.

Why Some Might Not:

While these are definitely chukkas, they don’t look anything like the original desert boot worn by the British army.

They run slightly higher up the ankle and have five pairs of eyelets (as opposed to just two or three), which makes them look less like chukkas and more like other types of ankle boots.

If you’re a stickler for that classic look, you’ll probably want to consider some different brands. The Clarks Original and Johnston & Murphy models below, along with the Beckett Simonon boot above, all look more like a classic desert boot.

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Best Casual Chukka Boots for Men ↓

Johnston & Murphy Copeland Chukka

Notable Features:

• Colors Available: 2
• Rubber crep sole
• Almond-shaped toe
• Have held up remarkably well after a decade of wear

Why We Like It:

Speaking as someone who’s owned two different pairs of Copelands for a decade now, I can tell you firsthand that this is a great option if you want classic style and all-day comfort.

I bought my first pair of Copelands back in 2014 in the red-brown color pictured above, and liked them so much that I bought another pair with tan suede uppers (which is unfortunately no longer available).

The Copelands have a premium leather upper that’s held up remarkably well over the years, but my favorite thing about them is the crepe rubber sole, which gives the boots a laid back, relaxed look while simultaneously providing great traction.

I also like how the toe box on these is just a little more almond-shaped than some of the other casual boots we’ve listed here, which sort of nods at style and sophistication without going full dress boot.

Why Some Might Not:

The big knock against Johnston & Murphy is that the uppers of their boots and shoes are glued or cemented, rather than stitched to the soles.

Stitched soles are generally preferable because the stitching creates a stronger and more durable seal, and stitched shoes are easier for a cobbler to resole when the sole inevitably gets run down.

(Although a good cobbler can resole a glued pair, as the guys at Cobbler Plus demonstrated on a pair of J&M side zips.)

But I’ve been pounding the pavement in my two pairs of Copelands for many years now and haven’t seen any separation between the upper and lower parts of the boot, even after a lot of wear.

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Best Men’s Suede Chukka Boots ↓

Church’s Ryder 3

Notable Features:

• Colors Available: 2
• Goodyear construction
• Worn by Daniel Craig’s Bond in Quantum of Solace

Why We Like It:

Delving into details of construction and material sourcing can sometimes overshadow a simple but fundamental truth:

The best desert boots – hell, the best clothes of any kind – are usually the ones worn by James Bond.

Church’s Ryder boots were originally designed for the desert terrain of South Africa, but among modern clotheshorses they’re best known as the stylish-as-hell boots worn by Daniel Craig’s 007 in Quantum of Solace.

With a timeless look that’s available in two different colors of premium suede leather (Bond rocked the deep brown pictured above), the Ryder is durable enough to chase down bad guys in the desert and stylish enough to meet Felix Leiter for drinks when the job is done.

Why Some Might Not:

The quality, style and double-O pedigree of these boots are all second-to-none, so the only real knock against them is the price.

At $1,100 they’re easily the most expensive boots on this list, and while the quality is undoubtedly high, most of us don’t have that kind of money.

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Best Cheap Chukka Boots for Men ↓

Bruno Marc Classic Suede Chukka Boots

Notable Features:

• Colors Available: 11
• Available in suede or leather
• Less than $100

Why We Like It:

Bruno Marc is known for making cheap AF extremely affordable shoes and boots, but after trying these ones out for myself, I have to admit:

This is a surprisingly decent pair of boots for the price.

With an excellent toe shape and a wide range of various colors, including the versatile gray color pictured above, it’s a particularly good choice from a style perspective.

And while you really can’t expect too much from boots or shoes that cost less than 100 bucks, it’s been a nice surprise in terms of value.

I definitely wouldn’t recommend them for trudging through snow in the depths of winter, but when the weather starts to warm up in early spring, they’re a good option for pairing with khakis or slim blue denim.

Why Some Might Not:

These perform remarkably well for $80 boots, but at the end of the day, they’re $80 dollar boots.

Low priced footwear like this is always a bit of a gamble in the quality department.

But my own take on Bruno Marc is that they hit a nice sweet spot between great style, low price and just-good-enough quality, so it’s a good option if you’re on a tight budget.

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Best Dress Chukka Boots for Men ↓

Beckett Simonon Fonseca

Notable Features:

• Colors Available: 5
• Italian, full grain leather upper
• Classic almond toe shape
• Upper made from calfskin leather and hand finished with carnauba wax and shea butter

Why We Like It:

Beckett Simonon’s Fonseca model is easily the best option if you’re looking for something dressy.

It has the same high-quality craftsmanship that makes the Laval pair listed above such a great value proposition – including premium Italian leather, Blake stitching, and Vachetta leather lining – but combines it with the kind of sophisticated almond toe shape usually reserved for a sleek pair of shoes.

The result is the rare leather chukka that can be paired with a suit and worn on formal occasions, including weddings, funerals and business meetings.   

Why Some Might Not:

We live in a casual world (much to my chagrin), and nowadays a lot of guys don’t even own proper dress shoes, never mind dress boots.

In my opinion the Fonseca’s toe shape and overall aesthetic is sexy as hell, but some might find it too “dressy” for their day-to-day style.

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Best Work Chukka Boots ↓

Red Wing Work Chukka

Notable Features:

• Colors Available: 2 (See the dark brown option here)
• Goodyear welt
• Full-grain leather upper
• Made in America

Why We Like It:

Red Wing makes some of the best boots for heavy-duty work, but what I love about their work chukka is how it straddles the line between performance and personal style.

At first glance, it has the same smart looks as the (rather handsome) Red Wing Heritage Weekender Chukka.

But whereas that boot is much more style-focused, with stitchdown construction and an oil-tanned leather upper, the Work chukka is Goodyear welted and has an upper made from full-grain leather, two little details that make it heartier and more durable.

Why Some Might Not:

This boot doesn’t have the safety features you’d find on a hardcore work boot, like a steel toe or an ASTM rating that denotes protection from electrical hazards.

It could be an excellent choice for architects or engineers who frequently visit job sites, but it’s not the best option if you’re a construction worker who spends all day in potentially hazardous conditions.

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Most Iconic Chukkas ↓

Hutton Playtime Chukkas

Notable Features:

• Colors Available: 2 welt colors available, but only one color of suede available for the upper
• Two-piece crepe sole
• Rich suede made from reverse calfskin
• Preferred boots of Steve Mc(F*cking)Queen

Why We Like It:

The Clarks below may be the most prototypical desert boot, but menswear doesn’t get much more iconic than the chukkas worn by the King of Cool himself.

McQueen wore these brown suede boots in some of his most famous and enduring roles, including both Bullitt and The Thomas Crown Affair, two of the most stylish and impactful menswear films of all time.

And it’s not hard to see what drew him to the Huttons.

Handmade in Italy, they have a thick crepe rubber sole that’s both durable and versatile, and a rich suede exterior made from reverse calf suede, which is actually thicker and more durable than regular suede because it’s made from the outer side of the calfskin.

Pair ’em with dark blue jeans and a chunky sweater for a damn-near perfect look come early fall.

But if you’re wearing the Huttons, you should probably resist the urge to throw on the Harrington jacket that McQueen also made famous.

Drawing inspiration from style icons is one thing, but wearing the full kit looks more like cosplay than sharp style.

Why Some Might Not:

These are only available in a suede exterior, so if you’re looking for a pair of the best leather chukka boots, you’ll have to look elsewhere.

They also only come in the one brown suede color, which is perfect for pairing with dark blue jeans or khakis (like McQueen did), but might not work as well if you prefer black jeans.

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Best Chukkas Boots for Wide Feet ↓

Cole Haan ØriginalGrand Chukka

Notable Features:

• Colors Available: 3
• Available in either Medium or Wide size
• Storm welted (Here’s what that means.)

Why We Like It:

These are another contender for the title of most comfortable chukka boots, which is no surprise from Cole Haan, because the brand has basically built its reputation on combining comfort with style.

But while the comfort level is certainly high, the appeal for wide-footed gentlemen is even higher.

Cole Haan offers almost all of their boots and shoes in both medium and wide widths, which is nice for guys who are used to feeling that pang of disappointment when they see a pair of kicks that looks great, but almost certainly won’t fit their feet.

In addition to the wide width, the other thing I like about this pair is that they don’t sacrifice style for comfort.

The toe shape is excellent, and the leather colors are rich.

The black pair, in particular, could easily be worn with a suit to formal events, while their British tan pair comes with a contrasting white sole that makes them a great casual boot to wear with jeans or chinos. 

Why Some Might Not:

The chunky rubber outsole may provide cushioning, but it’s not a great thing if you’re going for a sleeker, more stylish look.

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Most Classic Option ↓

Original Clarks Desert Boots

Notable Features:

• Colors Available: 9
• Serious pedigree (Clarks practically invented the modern desert boot)
• “Pebble” crepe rubber outsole gives it a rugged look

Why We Like It:

No list of the best chukka boots would be complete without the company that started it all:

Nathan Clark, the great-grandson of the founder of Clarks, is the man credited with inventing the modern desert boot, and Clarks chukka boots remain the gold standard for many. 

Personally, I prefer the Original Desert Boot to Clarks Men’s Bushacre model, another popular model that’s quite similar. 

But where the Bushacre has a faux crepe rubber sole and thicker cotton laces, the Original has a natural rubber sole and flat, waxed cotton laces, which in my opinion help elevate the look.

Plus, the Original is available in a whopping 9 different colors, including some pretty unique ones like navy and “cola” suede, which is why it’s always been one of my personal favorites. 

Why Some Might Not:

These boots were inspired by an old pair of desert sh*t kickers that Nathan Clark found at a bazaar in Cairo, and while it’s definitely a ruggedly handsome design, it’s undeniably casual.

But for more of a crossover style that can work in both casual and dressed-up situations, I prefer the Beckett Simonon Lavals.

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More Resources ↓

More Advice on Stylish & Comfortable Men’s Boots:

• The 9 Most Stylish Boot Styles for Men
• An In-Depth Review of Thursday Boots
• The 24 Best, Most Comfortable Work Boots
• The 11 Most Comfortable Mens Chelsea Boots
• Johnston & Murphy Karnes Cap Toe Boot Review
• The Best Red Wing Boots for Men to Wear Daily
• The 11 Most Comfortable Steel Toe Boots for Standing All Day
• The 17 Best Sneaker Boots for Men
• The (Absolute) Best Chelsea Boots for Men