The 20 Best Men’s Chukka Boots For Real Shoe Enthusiasts [2021 Edition]
The Perfect Every Day Shoe
Chukka Boots are the ultimate every day shoe for the modern man and should be in your wardrobe.
Which is exactly why I decided to write a comprehensive guide about the 20 Best Chukka Boots for Men in 2021. And when I say Best, I mean ones that actually deserve your hard-earned money.
If you want to skip straight to the action, please use the handy Table of Contents! I do suggest you read the next paragraph first though.
Grab a cup of warm coffee and let’s discuss Chukkas.
Not All Chukka Boots Are Equal
Most fashion and lifestyle influencers think a shoe is good just because it is “Goodyear Welted” or has “Full Grain Leather”.
While construction and leather grading is certainly an initial indication of quality there is much more to a good shoe than that. Cheap shoes are cheap because a manufacturer cuts corners in certain parts of the shoe.
So even if a shoe has a Goodyear Welt the leather can be loose grain or synthetic. On the other hand, a shoe might say that they use Full Grain Leather BUT it can be from the worst part of the hide.
The next time you stumble upon a guide that claims to show you the “Best” of any product be smart. Does a $150 shoe really have the potential to be the best in anything?
The 20 Best Chukka Boots Of 2021
Criteria for this list are quite simple. A shoe has to have good construction and excellent characteristics for its price tier.
A boot from Meermin will not be the best in the world but it certainly is great for the price you pay. I will also focus on RTW brands that are generally more accessible without longer waiting times.
1. Meermin 101468 Chukka Boots | $210
We begin by taking a trip to Mallorca in Spain. While probably the lowest quality shoe on this list there are few that can deny the value that Meermin brings at this price point.
For $210 you get a Goodyear Welted Chukka which is available in 4 colors and 2 leathers with a Dainite Sole and French Calf from Du Puy.
My personal pick is their 101468 Chukka Boots in Dark Brown Calf. It is the most versatile color for men and perfect for any casual day out.
It is an excellent starting shoe to enter the shoe world and barring the initial stiff break-in the HIRO Last is actually rather nice. My size advice for these is your regular UK size.
They will blow out of the water any other shoe brand under $200.
2. J.Fitzpatrick Whatcom Chukka Boots | $295
Justin Fitzpatrick is a shoe enthusiast whose Blog you need to read (Link to The Shoe Snob) if you love shoes.
He also sells his own shoes and they are usually a bit more adventurous when it comes to design.
In the recently released JF Line he introduced some more conservative staples for a man’s wardrobe and it of course includes Chukka Boots.
My pick is this boot in Blueberry Suede for the excellent price of $295. Justin makes these shoes in Spain with the traditional Goodyear Welt Method on a city sole.
Blue and Navy are very underrated colors when it comes to footwear but they are extremely versatile and fun to wear.
Not only that but when tastefully combined with the rest of your clothes it shows you care about your appearance and you have a sense of style.
The Whatcom – which is the name of the model – also has a gentle smart round last (Rainier) with a medium width and instep. The general advice is to get your usual welted footwear UK or US Size.
If you are not a big fan of this color there are others to choose as well.
3. Carlos Santos 7991 Chukka Boots | $309.99
When a Shoe Brand surprises you so much that you decide to quit your corporate job and work with them instead, it must mean they are good.
Portuguese Carlos Santos is no stranger to shoemaking dating back to 1942. They have a variety of lines but the quality really picks up with their Goodyear Welted Range.
My pick is a personal favorite which is exclusive at The Noble Shoe. A wonderful Dark Brown Goat Suede Chukka Boot with a Dainite Sole.
The step up in quality from Meermin and Allen Edmonds is astonishing especially considering the price of $309.99.
Sharp, elegant with superb leather and excellent construction these are one of the building blocks of your wardrobe. The texture is perfect for jeans, chinos and flannel and the color just makes them so easy to match.
These are on the 401 almond last which has a slightly elongated toe shape and a roomier instep. Perfect for those with slightly wider feet. My advice is half a size down from your regular UK.
If you are willing to spend a little more than $250 on footwear I recommend you from this list to try these first. They will really set a benchmark.
4. Sons Of Henrey Ambly Chukka Boots | $385
Sit down and notice, because this is a truly excellent brand you should know about.
Sons of Henrey is a very small brand specializing in Custom Made to Order Shoes in Belgium. My friend Tom is currently the owner and he has a long history and experience with shoemaking.
His Ready To Wear Selection is minimal and stock varies however the quality is undeniable for a fantastic price.
My pick (if you can find it in stock) is the Ambly Chukka Boots in Dark Brown Utah Calf. For those of you that don’t know about Utah Calf it is a form of pebble/scotchgrain although with a much more discreet pattern.
Supple incredible leather that you won’t find often in RTW shoes. It retains a classic shape with a slightly more tapered waist and a softer round toe.
When it comes to construction and attention that goes into the stitching and design it is one of the best in this price tier really. I can’t wait to formally review one of them.
There is no need for me to repeat myself about how versatile brown is but the leather adds so much elegant suave to your outfits.
Any of the shoes Sons of Henrey sells are worth considering. You’ll thank me later.
5. Crockett & Jones Molton | $419.99
When you think about James Bond you immediately think about finesse with a touch of badass. Which is exactly why I think this is a model worth of the title “Best”.
The Crockett & Jones Molton in Dark Brown Roughout Suede is the official shoe from the upcoming James Bond Film “No Time To Die”.
I could rave on for hours about how dimension defyingly durable this form of suede is. It’s all due to the waxy dense surface of the leather.
Crockett and Jones needs no introduction and are the quintessentially most British brand you need to know about.
The Molton has a rounder toe shape and a classy yet rugged look making it a fantastic every day shoe. It is especially interesting for those of you that might enjoy service boots such as Red Wings and Wolverines.
Goodyear Welted as all the shoes in this list with top of the line leather quality and a Dainite Sole on the 336 Last.
You can find these in most retailers around the world including the official Crockett & Jones shop. However you can always order it through me for a good price. I will appreciate it a lot!
6. Cheaney Jackie III R Chukka Boots | $425
Let us stay in the UK with a great British Classic. So far we saw boots in different colors and leathers however we now step it up a notch.
The Cheaney Jackie III R is for those that want a more elegant, sharp Chukka to dress up in style.
Entering the $400 territory it better be good too. Luckily my experience with Cheaney is excellent and their shoes have fair prices and great construction.
The details are good and there is a close attention to detail when it comes to the trimming of the lining, the welt and of course the stitching.
These Chukkas might be dressier but also sport a double stacked Dainite Rubber Sole for durability and urban environments. Goodyear Welted on the 125 Last which is fairly TTS (True To Size) in my opinion.
Admittedly I found their Black Grain rugged Chukkas also lovely but they seem to be out of stock at the time of writing.
7. Cobbler Union 312 Chukka Boots | $425
A small American company that draws inspiration from Bespoke Custom Shoemaking sums up Cobbler Union pretty well.
Their shoes are in a very competitive segment between $400-500 which is a testament to their quality. In these ranges if your shoes are not good enough you will not go very far.
My personal pick from this collection is their 312 Tobacco Suede Chukkas. Tobacco colored suede just looks so buttery soft doesn’t it?
And I assure you it will feel like that too with a soft nap and its excellent design. Here you can begin appreciating small design details such as the non-traditional yet tasteful line along the shaft and the discrete broguing.
On the back it also has a tiny detail nobody will notice which is a leaf shaped back seam. Two eyelets and flat laces are also small touches and if you notice the shoes seem to have a storm welt for added waterproofness.
This last is actually rounder with a wider feet making it perfect for those of you that have trouble finding wider shoes. Sizing advice is half a size down from your regular UK/US for those with regular width feet.
Certainly a more casual every day boot you can slip on and off at any time whether you go to the grocery store or have casual Friday at work.
8. TLB Mallorca Artista Chukka Boots | $445
This is a Brand you should know about and one of the best bang for buck brands right now.
TLB Mallorca is a fairly new brand out of Spain that makes incredibly good shoes that should honestly cost more. Their flagship Artista Line has features that are hard to find even at the high end shoes.
Whereas many shoemakers cut corners in many parts of the shoe, the Artista Line has great leather, real leather heel stiffeners and possibly one of the best city soles in the world.
Their new Chukka Boots have a Dark Brown color and a more unusual (but sexy) soft square toe. I recommend checking out my Review Here.
Don’t be afraid of the chiseled toes but they do tend to give a more elongated look. If you prefer rounder toes you can make a custom pair with the Goya Last.
As for sizing once more I found the Picasso to run rather regular width so choose your usual UK size.
9. Carmina 80697 Norwegian Boots | $445.85
If you thought the previous entries were classic then prepare yourselves for these!
Carmina is hands down one of the best shoemakers in the world. Also out of Mallorca in Spain (see the pattern here?) they have a reputation for quality.
As you can see we are already entering the higher end of shoemaking and I could not pass the opportunity to show off these Chukkas.
The 80697 is an absolute treat with a rather unusual design for a Chukka Boot. It has an apron and a split-toe for a very aggressive sexy design.
You are going to subtly turn some heads with these ones I promise you. Of course they are Goodyear Welted but also have JR Rendenbach Soles which are the best in the industry.
Closed-Channel Leather Sole with brass nails in the front and top leather and a very modern last.
The BALITX Last doesn’t have the sexiest name however it makes up for it with it’s looks. It also is be rather comfortable despite its slim looks with a slightly narrower fit to the Rain.
10. George Lyon Benjamin Boot | $460
Probably the newest and most controversial entry on this list is George Lyon Shoes.
Yet another small American business with a passion for shoes and a charming history. To learn more about them I recommend reading my full in-depth Review (Click Here!)
While their selection is super small and very special I can safely say that the Benjamin Chukka Boots are incredible. If you crave a more rugged “Americana” aesthetic but with better quality across the board look no further.
Superb pebble grain leather with great texture and a tough Norwegian welt construction coupled with a Ridgeway Rubber Sole make for an amazing boot.
The fit is good right out of the box (although with a little stiffer shaft) and it’s the sort of shoe you will want to wear whenever you can. If you love denim and heavier chinos this is a match made in heaven.
Perfectly balanced with a rich chestnut color for the ultimate casual Chukka Boots. The price might seem high initially but with George Lyon Shoes you get a premium unboxing experience with loads of goodies AND a matching belt.
Josh (the owner) is working on finding a way to offer the shoes without the belt which would make the boots even more affordable. A purchase you will not regret.
11. Antonio Meccariello Tribune 1 | $545
The more you learn about high end shoes, the more you will hear about Master Antonio Meccariello from Naples.
A true artisan making mainly Bespoke shoes but with some true Ready To Wear gems for you. My pick this time is the brilliant Tribune 1.
The Tribune is a classic round toe Chukka from calfskin suede in a gentle mid-brown color with reddish hues. It adds just a little bit of depth and flair to them.
Antonio makes this in a very special way called “Argentum” which is a mix of Goodyear and Hand-welting. Top notch construction with a very tight waist and a leather sole finished with a Vibram insert.
Getting your hands on Meccariello shoes will help you truly understand why “Handmade in Italy” is so important for brands.
Needless to say that this is a great Chukka Boot for casual wear and usable for at least 3 seasons per year.
12. Caulaincourt Solognac Boots | $592
Onwards to France for the next two entries! When researching for this article I often stumbled upon the classic Clarks Desert Boots.
Unfortunately those boots are not worthy of your money these days with cheap construction and materials. However khaki and beige sandy colors seem to be very popular for these types of boots.
The one I found and picked my interest was the Solognac Norwegian Boot by French Caulaincourt. You can see by the price that this should be a high quality shoe.
It is not only tasteful with nice curves and design lines but also has superior construction. A full classic Norwegian 360 welt with those trademark serrated edges.
Finished in buttery smooth taupe suede (zoom in the pictures to really see the texture!) and a natural sole for a casual urban look. The Solognac is on the 1827 Last with a gentle almond toe shape.
Caulaincourt is a brand that often flies under the radar and you should totally check them out.
13. Altan Bottier Arthur St. Moritz | 596$
Looking for something chic and extravagant at the same time? Then the Arthur by Altan Bottier is an amazing option.
Altan Bottier has one of the most recognizable design style in the welted shoe market right now. There is a strong focus on exotic leathers and heavily burnished patinas.
Chic, emblematic, daring and casual, the Arthur is an unusual take on Chukka Boots. It is also the only Blake Stitched shoe on the list and commands a premium price but you get what you pay for.
Its Commando soles give a surprisingly not so chunky but sharp appearance finished with a faux storm welt on the top. In yet another unusual move Altan pairs them with a soft square chiseled toe for the ultimate look.
Who would have thought! However it works really well and you will spot a few details here and there such as the speed hooks instead of eyelets.
Brilliant design available in 9 handpainted patinas (more upon request) including the Green Autumn Leaves Patina in the picture.
14. Zonkey Boot 055 Toscano Chukkas | $818
We are now entering what I call the endgame with Zonkey Boot.
Don’t let the silly name fool you because this brand came from one of the original founds of Saint Crispin’s. High end shoes with impeccable construction, materials though often with designs that are not for everyone.
One of their Best Chukka Boots is the 055 Toscano model in gorgeous high-gloss Bavarian Calf in a brown chestnut finish.
These shoes are hand-welted and hand-lasted with a high quality closed channel leather sole. They sport two eyelets and have a very minimalist design without much of a fuss.
The trimming of the welt is extraordinarily tidy and I like how they went for a more natural finish on the outsole.
For those that want something classy, classic and minimalist it’s a great option.
15. Mario Bemer Bacco Grey Suede | $1182
The word Best and the Bemer shoemaking family in Italy go hand in hand.
Mario is the brother of legendary shoemaker Stefano Bemer (next on this list) and his designs are unique and daring.
His Bacco Chukka Boots in Light Grey Suede are sublime and my pick for this price tier.
If you are a fan of Tom Hiddleston you probably know how much he loves his grey boots. And I am pretty sure you will love yours too!
Certainly a statement of intent and fashion piece but not too extravagant with discrete contrast stitching and beautifully trimmed welt and sole.
I especially like the delicate shaft and discrete cap-toe on the front and the lovely touch of brown flat laces.
This is a fantastic shoe for the money and its uniqueness.
16. Stefano Bemer 7000V1 Waxy Kudu Chukkas | $1350
I already mentioned how important the Bemer family is in the shoe world.
It is a little more complicated than that so let’s focus on the task at hand! If you want you can Read more about them here.
The next Chukka worthy of the title Best is this smashing Waxy Kudu Boot called the 7000V1.
What makes this unique is the choice of leather which is Kudu (African antelope).
It is a type of exotic leather that is extremely supple yet incredibly durable. It also has natural markings and scars on the hide which are results of the animal’s life in the wild.
Perfect for those that favor texture and natural patina with a construction second to none. Welted in Italy with a slim city rubber sole and durable uppers.
In the price you also get lasted shoe trees and a custom wooden box for a luxury experience.
These Chukkas are on the T Last which is especially good for those with a lower instep, good arch support and less voluminous feet.
Kudu is one of my personal favorite leathers and you should try it at least once in your life.
17. Saint Crispin’s 524 Shrunken Calf Chukkas | $1500
Many companies say their shoes are handmade yet very few really are.
Saint Crispin’s from Transylvania are a rare dying breed of shoemakers.
Even though I don’t often like their style and the tons of filters they use on their pictures I cannot argue they are incredible shoes.
There is something very attractive about unique leathers on Chukka Boots and this model is no different. The Saint Crispin’s 524 has some vintage shrunken calf with a remarkable, dense grain texture.
It goes very well with the casual comfortable rubber sole they use and the color is versatile. The design is also as simple as it gets with 2 eyelets and a sharp toe because the emphasis is on the leather here.
Real quality for a premium price like no other.
18. Paolo Scafora Art. St54 | $1524
One of the best shoemakers in the world and my personal revelation for 2020. In fact I hope I can be an apprentice for this legend.
Paolo Scafora has a small workshop in Naples (Italy) and specializes in designs and a style that will grow you chest hair.
Very sharp chiseled toes and the finest leathers as well as his impeccable Norwegian and Tyrolese constructions.
For this list I chose the Paolo Scafora Art. St54 Chukka Boots in a cognac/whiskey color. They take the classic desert boots and up the ante with an incredible triple braided welt.
This is the only shoe on the list that is available as Made to Order but with a 4-6 weeks waiting period it is perfectly fine to wait for such quality.
You can customize things like the sole, color and shape and even add your initials. Everything is handmade and handpainted and truly worthy of the word Best.
The Noble Shoe also retails a few models of Paolo Scafora. Check them out here!
19. Edward Green Banbury | $1530
When someone talks about the best in any shoemaking category it is hard not to mention Edward Green.
An iconic British shoemaker with reputation for high quality and the quintessential English Style.
I feel a pair of brown suede chukkas should be in every man’s wardrobe and their Banbury model in Taupe is simply a delight.
Goodyear Welted in Northampton (the hub of shoemaking) on velvet soft brown suede and a Dainite Sole. Finished on the contemporary 202 Last.
What a joy to live in times like these when the options are so many. Such an elegant shoe with just the perfect tone of brown.
It will go with jeans and contrasting chinos extremely well.
20. John Lobb Alston In Black Calf | $2,170
Finishing off the list with a difficult brand to recommend due to pricing but one that carries considerable heritage.
John Lobb shoes won’t strike you as stunning or dashing very often with a rather conservative style. My choice is nothing but usual though,
The John Lobb Alston is a phenomenal mix of a derby split-toe boot and a chukka. Finished in high-polished black calf with probably the best leather in the world.
Meticulous details all around the shoe from the apron to the way the stitching meets the top of the shaft. It doesn’t even have a backseam and the “split-toe” is invisible under the leather.
Superb shoes and if you are on the hunt for the best and money is not an issue this might be the one.
Every “Best X” List is entirely subjective and taste differs. So here are a few honorable mentions and alternatives for those of you that might enjoy different styles:
- Grenson: Chunkier more country style shoes. Made in India
- Loake: Classic British Shoes for a fair price. Stick with their 1880 or Export Grade Lines
- Myrqvist: Swedish minimalist brand that makes shoes in Portugal. Service could be better
- Yanko: Decent Spanish Brand for a fair price. Buy only through Skolyx for good service
- Red Wing: Classic American Brand. Perfect for those that value durability and “work wear” over aesthetics
- Alden: One of the last bastions of quality US Shoemaking. Usually tanky styles specializing in Shell Cordovan (Link to Alden Madison)
- Allen Edmonds: Diminishing quality since 2013 but still a decent option if you really want to support a US Product
- Thursday Boots: Not a massive fan of these but they are fair for the price point if you don’t expect the best
- Rancourt: Traditional small US company from Maine. They have some nice more casual Blake Vegetable Tanned Chukkas
Missing any? Let me know in the comments or send your suggestion to email@example.com!
Chukka Boots | Brands To Avoid
There are also some brands that I cannot recommend of course. These are mostly in the lists of most Google articles and you should be very careful:
- Nisolo: A few customers said it was like “wearing a cardboard box“. Made ethically but you can do better
- Timberland: Bonwelted, cemented and low quality riding a vintage name. Don’t buy them
- Ace Marks: The amount of marketing that goes in these is incredible. Not a bad shoe but Blake Stitched and definitely not a $600 shoe for $300
- Paul Evans: See above. Their wholesale is around the $150 mark I’d say and the leather is thin and not exactly high quality
- Clarks: They are not what they used to be. Low quality and there are far more stylish options out there
Of course there are many more. Want to learn more about them? Read my Worst Brands Article!
How To Clean & Maintain Your Chukka Boots
One of the most important things you need to do is taking good care of your shoes.
It is actually quite easy and fast to ensure that they are always in great condition. Let’s begin with a few basic tips that apply to all of them:
- Rotation: A good rule of thumb is to let a pair of shoes rest for 24-48 hours after each use. It let’s the leather rest and return to shape and will prolong its life
- Shoe Trees: You don’t need fancy shoe trees or boot trees. Regular Cedar ones will do the job well and minimize creasing
- Avoid Heat Sources: Do not leave your shoes in direct sunlight or next to radiators. The leather will dry and crack. If they are wet simply wipe gently with a cloth and let them dry
Now let’s discuss some tips for each leather type.
How To Take Care Of Suede Chukka Boots
Contrary to popular belief good suede is rather resilient and easy to take care of. Here are some tips:
- Waterproof Spray: Spray them once or twice a year with Saphir Super Invulner
- Suede Brush: Suede uses special affordable brushes to restore the nap and clean the dirt. Regular shoe brushes might damage the nap so be careful
- Suede Shampoo: If you stain your suede chukkas you can use special suede shampoo, brush them and let them dry
If you want to know more on the subject check out this video:
How To Take Care Of Calf Chukka Boots
If you are really short on time or don’t want to bother much with shining it is ok. You will need some tools though:
- Horsehair Shoe Brush: Use it to buff polish and wax as well as remove excess dirt from your shoes
- Cotton Cloth: A polishing chamois or a simply white old cotton t-shirt is enough to help you apply the polishes
- Cream Polish & Wax: If your shoes are handpainted make sure to use neutral colors. Otherwise a colored pigment closest to the color of the shoes
Quite simple isn’t it? I can recommend a step-by-step guide by Andy from Pure Polish (Article Here) or the following video:
How To Wear Chukka Boots
Chukka Boots are a casual type of shoe by nature. Since the Prince of Wales wore them in a game of Polo in 1924 they became a sensation.
A really versatile and easy to wear shoe that is perfect for casual and smart casual style.
For most of you it means that you will wear them with a nice pair of jeans or cotton chinos. You can complete the look with a nice button down or flannel shirt (depending on the season) or why not linen in warmer weather.
For casual and smart casual wear you can never go wrong with smooth calf leather. However waxy calf, bison, kudu and suede are perfect to give little more oomph to your outfit.
When combining textured leather with clothes remember to add some form of texture to them too!
Can I Wear Chukka Boots With Suits?
The general consensus is that you should not wear Chukka Boots with formal attire.
In some cases a really nice minimalist Chukka with smooth calf leather might be fine for a suit.
Personally I avoid doing that however I find it is more than acceptable to wear them with some separates or a more casual flannel suit.
If you do decide to wear Chukka Boots with a business suit make sure it is appropriate attire for the occasion. In such cases do not wear anything else but smooth calf boots or it will look sloppy and out of place.
Chukka Boots Vs Desert Boots
This is a section that deserves its own article! But I will make a brief mention to this commonly asked question.
The original Desert Boot had suede uppers and a crepe sole and were very popular for soldiers around the WWII era.
Due to the association of the style with lower class citizens the official launch of the original Clarks was around 1950.
Today’s Chukka Boots however are much more versatile and way more modern. They come in different leathers and fabrics as well as rubber or leather soles.
Desert Boots on the other hand have a more rough appearance and thicker sole to match their formality.
Chukka boots today have become far more versatile than the originals and have been stylized to suit the times. The differences in the finer style details of the boot today determine whether they are right for business or leisure.
In many ways you could say that Chukka Boots are an evolved version of Desert Boots.
The Best Chukka Boots For Men In 2021
There we have it! A very important Guide for me and hopefully one that will help you in your quest for the Best Chukka Boots For Men In 2021!
We covered some fantastic brands, gave some alternatives and even discussed about taking care of your Chukkas.
If you found this Guide helpful please consider sharing it and as always your comments will mean a lot to me!
I enjoy greatly writing these types of article and I will surely be back with similar ones for Chelseas, Oxfords and more. In the meantime, be safe and if you are new please Subscribe to the Newsletter!
Thank you for reading,