5 Best Waterproof Chukka Boots for Men Reviewed with Buying Guide

  • By: Vishal Mahadik
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​I am sure you will definitely agree with me when I say this:

"Chukka boots look really stylish with a jeans and t-shirt. No matter what casual looks you want to showcase, these Chukka boots perfectly fit your smart casual style."

So, today I am going to discuss about them. But particularly about the best waterproof chukka boots.

If you are preparing for rainy seasons, want to enhance your fashion and style, or simply looking for appropriate footwear for your everyday commute, then these boots are simply the best choice for you.

You can wear these boots in almost all kinds of environments and in all types of weather conditions. This is a range of footwear that is designed mainly to conquer adverse weather.

Other than that, it can also enhance your looks and appearance. Lastly, some of these boots are also light and sturdy enough for everyday commutes.

In this article, you will learn more about the best choices for waterproof chukka boots. I will also share an extensive buying guide that will help you to finalize the best boot for your requirements.

I am sure these boots will offer you the opportunity to look yourself cool and stylish.

Also, the buying guide will help you to pick the best one from various brands which manufacture these boots.

​Buyer’s Guide to Help You Choose the Top Quality Waterproof Chukka Boots

​Before you go and buy any boot from the market, it is really important for you to know the best features and some knowledge about these types of boots.

So, I am providing answers to some of the most frequently asked queries by users on the internet. I hope you will find them resourceful.

​Are Chukka Boots Really Waterproof?

Timberland Men's Waterproof Chukka,Brown Smooth,US 10 W

The short answer is “Yes”, they are!

They are as a matter of fact; purposefully intended to conquer extreme weather conditions.

This happens because all of its crucial parts have waterproof materials constituting the boot.

Examples of these are the sealants which fix the seam and a couple of other waterproofing substances.

What’s more?

Their shafts are for a large part; a bit longer. They stretch from the heel to the arch.

This way, they cover your entire feet and lower legs. You will hence find them particularly handy for walking in rainy, snowy and moist conditions.

​How to Waterproof Chukka Boots?

​Just in case your Chukka boots are not waterproof, you need not have to worry at all. It is indeed possible for you to waterproof them.

For you to do this, you will have to bring in some extra parts and substances.

You may, for instance, seal the seams, overlay a suitable Hydro-Shield® waterproofing substance atop the sole, or spray some sealants.

You will definitely have to bring in an expert to help you out. This is a complex undertaking which you cannot attempt on your own.

So, I recommend taking guidance or help from a professional regarding waterproofing your new or old Chukka footwear.

​6 Primary Features to Look for When Buying Waterproof Chukka Boots

Rockport Men's Essential Details Waterproof Dress Chukka Black 6.5 M (D)

1. Weather Resistance

The weather varies greatly from time to time and place to place. It cannot always be easy for the pair of boot you wear has what it takes to tackle that weather.

That is why you have to be sensitive to the kind of pair you lay your hands on, with regards to this. The Chukka boot you will wear must provide your feet proper breathability and protection from outside heat and humidity.

2. Grip and Traction

Traction refers to the grip of your boot sole which provides more stability and support while walking on slippery grounds.

Needless to say, the Chukka boot that you wear must offer excellent traction. You do not want to skid, lose balance, or fall off while walking, do you?

So, my recommendation is to look for the boot that comes with sole having good grip and traction for all kinds of surfaces.

3. Good Support and Foot Protection

Just like every boot differs in its construction and stature, so do the various kinds of feet.

If yours is a sensitive or very painful foot, you need to mind the support you are bound to receive from the pair.

The pair you settle on has to be equipped to provide added support and higher foot safety features. Most Chukka boots do come with sufficient protection for your ankles, heels and toes.

4. Comfortable Fitting

It is a common knowledge that shoes and feet come with different sizes, widths and lengths.

Putting on a pair that is either too large or too small for your feet is definitely a recipe for disaster.

The best Chukka boot has to be as compatible with the size and shape of your feet as nearly as possible.

That is why, you also need to know your correct foot size and width so that you can get the right fitting boot for your feet.

5. Enhanced Comfort

While walking in these Chukka boots, you want to be more comfortable and relaxed.

You do not want to confront bruises or any other common foot ailments such as bunions, peroneal tendonitis or plantar fasciitis.

This can only happen if you pick comfortable pairs of boots. The interior has to possess a lining can reduce any possible friction or vibrations.

6. Improved Breathability

Lastly, you also want the pair you choose to be highly breathable.

You do not want your feet to be smelly after walking in them for long period of time.

You need to make sure that the pair you have in mind is manufactured using fabrics that have larger pores.

Nylon and polyester are the two best materials of that offer highest breathability. So, look out for these materials when checking out the features of the Chukka boot.

​What are the Best Brands That Produce Waterproof Chukka Boots?

​1. Clarks 

Clarks is a British-based shoe manufacturer. This company deals mainly in those Chukka boots which are intended for general wears.

That is evidenced by their ability to produce their first Chukka boot in the 1950s. First the company started manufacturing lightweight and comfortable boot with rubber soles.  

The style has not been changed a lot since then. Most of these Clarks Chukka boots are affordable and not so expensive.

Some of the most popular chukka boots from Clarks are Clarks Men’s Desert Chukka Boot and Men’s Bushacre 2 Chukka Boot.

I have written a guide about best Clarks desert boots. Click here to check it out if you are interested in desert boots.

2. Timberland 

Timberland is a well-known American boot manufacturer brand.

This one specializes in manufacturing fashionable garments and boots. For this reason, its range of clothing and footwear are costlier than the average counterparts.

But its specially manufactured Chukka footwear have distinctive eyelets on the upper and signature Timberland design.

If you really like this brand, then you will definitely love Kendrick Men’s Waterproof Chukka Boot and Women’s Nellie Waterproof Chukka Footwear.

3. Rockport 

Rockport is yet another American manufacturer of Chukka boots.

Its range of boots is mainly geared for extreme weather conditions. You can wear them comfortably in extreme weather situations such as heavy snow or heavy rainfall.

You will find its product range quite durable and heavy to wear. Some of the most popular chukka boots from Rockport are Essential Details Waterproof Chukka and Classic Break Chukka.

4. Skechers

Skechers is a well-known authority in the field of lifestyle and performance boots.

It is primarily based in the USA. You will love this brand a lot if you value class and elegance.

Also, the range of footwear may be really helpful to you if you are an athletic person.

Some of the most well-known Chukka boots of Skechers are Men’s ​Segment Melego Leather Chukka Boot and Men’s Recent Handler Chukka Boot.

5. Calvin Klein 

Just like Skechers above, Calvin Klein is yet another authority in the field of lifestyle and performance.

In particular, its range of boots is great for luxury and lifestyle fashion. They are by far the most expensive in the category of waterproof Chukka boots.

The most popular ones are Men’s Ulysses Suede Chukka Boot and Men’s CAM Tumbled Leather Chukka Boot.

​Reviews of Top 5 Waterproof Chukka Boots

​No. 5: Dunham Men's Revdash Waterproof Chukka Boot

Dunham Men's Revdash

​Are you a person who devotes much of his life running errands? If you are, you desperately want to lay your hands on this Dunham Rev​dash Chukka Boot​.

That is because it is intended for regular walking. At the same time, it is also stylish, a fact that makes it fair to behold.

Comprising some full-grain leather upper, this pair is pretty durable. The material lets it stand to the most severe impacts.

Further, some sleek silhouette adorns the exterior layer of the leather. This one enhances the appearance of the entire boot as well. This is besides the riveting Dunham® REVdash.

All the stated parts and features are joined together with some enduring stitches. The eyelet lacing is extensively used to join these two parts together.

In all, the stitches alternate between the light and the contrast ones. The end result of this kind of arrangement is some beautiful seams.


​Effective moisture management

​Removable TPE and memory foam footbed

​Delivers added comfort

​Provides excellent arch support

​Promotes stable strides


​Requires tedious cleaning

​Not for muddy conditions

​No. 4: C​larks Men's Truxton Top Chukka Boot

CLARKS Men's Truxton Top Chukka Boot

​If you value style and fashion, you definitely want to wear only those boots which have been trusted to deliver just that. Look to no other boots than this Clarks Truxton Footwear.

Indeed, this pair has been in existence for well over 100 years. Many have been praising about its awesome durability.

Setting this pair apart from the others is the rubber sole. The sole, courtesy of the rubber construction, is both strong and agile.

By reason of this arrangement, it yields you years of reliable operations. While at it, the outsole does not compromise your agility in any shape or form.

It does have an extraordinarily long shaft. This measures a whopping 3.93 inches and stretches all the way from the arch to the heel.

It covers the lower portions of your feet sufficiently. This it does while seeing to it that the covered portions do not sustain any serious injuries.


​Waterproof design and stature

​Cushioned soft insole

​Classic styling

​Non-marking outsole

​Ortholite footbed


​Too much care and maintenance needed

​Quite bulky to walk in

​No. 3: Sorel Men's Madson Chukka Waterproof Boot

SOREL - Men's Madson Chukka Waterproof Boots, Suede, Crouton, 7.5 M US

​A good boot should go beyond merely covering your feet. Ideally, the boot of choice has to exude some aesthetics as well.

The manufacturer of this ​Sorel Madson Chukka Boot understands these two facts well. That is why it has ensured that this boot incorporates both elements in one comprehensive package.

The boot features some die cut EVA midsole. Inside this midsole, you will find the full-length EVA lining being inserted which offers higher comfort.

The objective of these two parts is to make your feet as comfortable as possible. They also minimize the direct contacts of your feet with the boots.

This way, they minimize the likelihood of bruises which is possible when walking and running in them.

Definitely, you will have to wear your boots for the longest realistic duration of time. This is especially true if you want to enjoy the highest returns on your investment.

Yet again, these boots make this happen. They have a molded rubber outsole which is pretty strong and highly durable too.


​Stylish silhouette design

​Waterproof suede upper

​Seam-sealed waterproof construction

​Synthetic inner lining

​Removable molded footbed


​Some parts of the boot are not very durable

​Lacks stronger foot stability

​No. 2: Rockport Men's Essential Details Waterproof Dress Chukka Boot

Rockport Men's Essential Details Waterproof Dress Chukka Black 6.5 M (D)

​Is your search for the right pair of boots mainly driven by the need to conquer wet weather? ​Then Rockport Essential Details Chukka Boot​ in the one you should look up to!

They lay claim to this fact by reason of their possession of the special seam sealant. This sealant shields the joints from letting in any moisture in wet weather conditions.

Its suitability for conquering wet weather does not stop there. Further, this pair is equipped with Hydro-Shield® waterproofing substances.

These are tanned into the leather and reinforce the ability of leather material to ward off the intrusion of moisture.

These boots perform a good job of keeping your feet moisture free regardless of the exterior moisture content.

As you walk out and about in this pair of boots, you will also enjoy massive foot support. This is made possible by the Polyurethane outsole.

The outsole provides some lightweight yet durable support. Chances of you fidgeting, tripping, or losing stability are hence suppressed to the maximum possible extent.


​Adjustable secure fitting

​Yields higher comfort

​Offers durable cushioning

​Active air circulation technology

​Maximum shock absorption


​Not much efficient for dry weather

​Easily sustains prickling

​Check out the following short review video so that you will know how the boot looks like in real life.

​No. 1: Timberland Men's Premium WP Waterproof Chukka Newman Boot

Timberland Men's Premium WP Chukka Newman, Wheat, 7 M US

​Are you preparing for a flood? If you are, this Timberland Premium Newman Chukka Boot is the pair to look up to.

That is because it provides adequate protection to your feet, heel, and arch.

Its long shaft that stretches from the ankle to the arch makes this possible. This is besides its waterproof qualities.

Among most unique features; there is this premium leather upper. This is derived from the LWG Silver-rated tannery.

It lasts longer than most other kinds of leather material. Also, this leather is more effective at warding off the intrusion of water into the pair’s interior.

In so doing, it shields you from unnecessary dampening.

Some seam-sealed construction also adorns this pair. The seams of the pair are basically reinforced for added strength.

This makes it stronger and better-placed at providing the needed support on a rainy day. Further, the reinforced seam also goes a long way in reducing your costs of repairs and maintenance.


​100% durable leather

​Stronger rubber sole

​Padded collar for high comfort

​Nylon shank for good arch support

​Prevents moisture and keeps your feet dry


​Limited lifespan

​Heats up easily

​Check out the following short review video to see the boot up close.

​Bottom Line

​There you have it! These are my top 5 most recommended waterproof chukka boots.

I have researched extensively just to find the most durable, comfortable and most waterproof Chukka footwear for you guys.

I am now fully confident that you have what it takes to make the right purchasing decision.

What else are you waiting for? Simply read the buying guide and pick the right boot from this list which meets your expectations.

I wish you best of luck in your search!



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