Success usually comes to those who are too busy to be looking for it.Henry David Thoreau

5 Best Waterproof Chukka Boots


Most recommended
Clarks Mens Bushacre 2 Chukka Boot
  • 100% Leather
  • Imported
  • Synthetic sole
A good choice too
Skechers Mens Segment Melego Leather Chukka
  • Color: Dark Brown
  • 100% Leather
  • Synthetic sole
A good choice too
Dr. Martens Bonny Chukka Boot
  • Leather/Nylon
  • Color: Black Extra
  • Synthetic sole
Steve Madden Mens Harken Chukka Boot
  • 100% Leather
  • Synthetic sole
  • Color: Black
Timberland Mens Kendrick Waterproof
  • Color: Black Full-grain
  • Imported
  • Rubber sole

Choose the Best Waterproof Chukka Boot

Customer’s Choice: the Best Rated Waterproof Chukka Boots

10 users answered this survey. Please help us improve this review!

30.00% of users selected Clarks Mens Bushacre 2 Chukka Boot, 20.00% selected Skechers Mens Segment Melego Leather Chukka, 30.00% selected Dr. Martens Bonny Chukka Boot, 0.00% selected Steve Madden Mens Harken Chukka Boot and 20.00% selected Timberland Mens Kendrick Waterproof. Every month we analyze your answers and change our rating.

Waterproof chukka boots are a great addition to any wardrobe. They’re especially useful in the fall and winter when it’s wet outside, but you still need to walk around with your head held high. In this guide, we will cover everything from how waterproof they are, to what kind of boots work best for keeping your feet warm. Keep reading for some helpful tips on how to find the right boot for you!

Clarks Men’s Bushacre 2 Chukka Boot

These Clarks Men’s Bushacre 2 Chukka Boots are the perfect footwear for any occasion, with their versatile appeal and casual styling.

They’re made of 100% leather; imported; come complete with a cushioned insole; feature chukka boot silhouette, two eyelets lace-up front, and platform measure approximately 0.75 inches from arch to the sole. With a unique finish or polish on these boots showing marks that are not scratched, they can be worn as easily dressed up as down!

  • Made of 100% leather
  • Comes complete with a cushioned insole
  • Can be worn as easily dressed up as down!
  • Many colors available

  • Can be expensive
  • Not the most comfortable chukka boots

Skechers Men’s Segment Melego Leather Chukka Waterproof Boot

You don’t have to be a hunter anymore with the Men’s Segment Melego Leather Chukka Waterproof Boot from Skechers. Fashionable 100% leather, rubber outsole for protection and grip?

You’re covered in this boot that plays nicely in both wet and dry conditions. Built-in comfort technology will leave you feeling like you’re walking on a cloud all day long too!

  • 100% Leather
  • Imported
  • Rubber sole
  • Comfortable

  • Sizes run small
  • Insoles not removable

Dr. Martens Bonny Chukka Boot

Take on the big, bad world in these Men’s Segment Melego Leather Chukka Boots – they offer nothing less than perfection. You’ll need durable protection for your feet with full leather uppers and extra-tough nylon that will give you the stability you need to tackle anything day after day.

Features include synthetic sole which gives you lightweight comfort without compromising on support, Dr. Martens air-cushioned sole so your feet feel like walking on clouds all day long, classic and durable sidewall stitching construction so your boots will last a lifetime of wearings, and finally but by no means least water-resistant padding keeps you more comfortable when crossing some pesky puddles!

  • Durable
  • Comfortable
  • Lightweight
  • Cheap

  • Only 3 colors are available
  • Runs slightly small

Steve Madden Men’s Harken Chukka Boot

The Steve Madden men’s Harken chukka boots are the perfect example of high quality and attractive design.

With imported, 100% leather material and a man-made sole with great traction strength, these boots will stand up to many years of wear without falling apart. These rugged shoes are part of Steve Madden’s diverse footwear inventory which also includes sneakers and oxfords for everyday business wear as well as jackets for those cold winter days at work or home!

  • 100% Leather
  • Textile lining and insole
  • Good traction and grip on the sole
  • Durable

  • Not very comfortable
  • Slightly tight

Timberland Mens Kendrick Waterproof Chukka Boot

Think of these boots as your rainboots of the future. Say goodbye to leaked shoes, splashy messes, and ruined clothes.

These babies are imported from quality full-grain leather with an upgraded defender repellent system that delivers superior stain resistance on top of Timberland’s waterproofing technology. When it rains, you’ll want to wear these men’s chukkas year-round! You can feel confident knowing this boot is ready for anything – whether you’re kicking back poolside or tackling rough terrain

  • Rubber sole
  • Full-grain leather
  • Durable
  • Lace-up closure

  • Expansive
  • A bit heavy

Buyer’s Guide

Benefits of Waterproof Chukka Boots

These boots are great because they provide the same benefits as regular chukkas, but with an extra layer of protection against water damage.

  • The boots are waterproof, so they won’t get ruined by water.
  • The boots are durable, so you can wear them for a long time without breaking or cracking.
  • Great for casual or formal outfits.
  • Lightweight and comfortable to wear all day long.
  • Easy to clean, just use a damp cloth.
  • Many different styles and colors for men of all tastes.
  • They come in both low and high-top designs.

Waterproof Chukka Boots can be worn casually or formally, making them a versatile shoe that matches any outfit choice. Not only are they super comfortable and lightweight to wear all day long but easy to clean as well. Don’t wait another minute – check out the selection today!!

Things to Consider When Buying Waterproof Chukka Boots

There are a lot of factors to consider when purchasing your pair of waterproof chukka boots. You must choose a boot that fits well and will last for years to come. So let’s take a look at some of the specifications that you should consider when purchasing your next pair.

Waterproof Rating

The first thing we all need to do before we even go shopping is check what waterproof rating our old boots have and look for a boot with equal or higher waterproofing. The waterproof rating is usually stated in millimeters and shows how deep water you can stand before your feet get wet.

For example, if the boots of interest to your state protect up to 20mm (which means about 600g/m) of pressure then go for a boot that protects a higher or equal amount because it will be way more durable and comfortable. The last thing we want when we are out there on our favorite hiking trail is getting some problems with our footwear and having cold wet socks and sweaty feet but this won’t happen anymore! So choose wisely based on the protection level given by the manufacturer otherwise your next pair might not do its job properly even though you spent good money on them!

The waterproof rating is important because you need to know how deep water your boots can hold before it starts seeping through the leather which will cause your feet to get wet. Of course, some boots are more waterproof than others and some water doesn’t even seep through the basic structure of the boot if it’s not too deep but you should still be careful as there is no point in buying a pair of expensive boots only for them to wear out after one winter season due to poor quality or negligence on your part.

Waterproof Rating: 2000mm-3000mm

For example, this rating means that if we immerse our shoes completely into 100cm (vertically) of freshwater it won’t penetrate until 2000mm (~79in). However, if we stand horizontally with half our foot immersed at 500mm (~20in), then the same amount of water will reach the top of our boot.

If you are planning on using your new boots for heavy hiking in deep snow or sporadically through spring, fall and winter then this rating is enough to keep your feet dry but if you want more protection then choose a higher waterproofing level otherwise it might not be worth spending that extra money!

Moreover, if your old waterproof chukka boots have a ‘waterproof membrane’ make sure to check where this membrane is located as it should be between the lining (which you might want to replace for better insulation) and outer shell otherwise it will not work properly.

If there are no indications on Amazon or other stores about the location of the water-resistant layer then contact the manufacturer directly! Don’t worry because they usually reply within 24 hours but first take into account that some manufacturers place their membranes in different parts depending on the model so you should consult with them before making any purchases. For example, Columbia Sportswear’s Outdry technology features an external, waterproof, breathable barrier.

Now that you have done this research, there are some other things worth mentioning. First of all, for most people (and especially UK residents), the biggest issue is finding a good quality boot with more than 25mm waterproofing at an affordable price. With prices on Amazon starting from £38 and many models available in different colors!

Another thing worth noting is that feet expand when they get wet so if the boot fits perfectly dry but not wet or tight after drying out then go up one size for best comfortability. However, never buy larger than your actual shoe size because besides looking funny as heck wearing too-big boots, it can lead to serious foot problems.

Leather Type

The next aspect to consider is the type of leather used. The most commonly used material for waterproof chukka boots is full-grain, aniline, and oil-tanned leather.

Full-grain is made from one continuous piece without any layers or splits which makes it more durable than other types of leather and will age nicely with time as its natural oils can be replenished over months if they dry out through wear and cleaning.

Aniline refers to hides that have not been sanded nor had their surface pigments removed before being dyed in the tanning process. This method allows them to retain all their natural markings while having a very light coat applied so you get lovely coloration throughout each boot. It also means there are no protective topcoats or sealants which makes them easier to maintain.

Oil-tanned leathers are the most water-resistant type available since they have been treated with oils and natural fats that fill in all of their pores, creases, etc. This thick coating keeps moisture out much better than other types but can make it harder to clean up if you happen to spill something on your boots by accident. The downside is oil-tanned materials will feel a little less flexible due to this treatment so if you drag your feet when walking around these may not be right for you as they tend not to bend very easily compared with others like full-grain.

It is up to you what type of material you prefer but knows that full-grain tends to be favored by those wanting durability, aniline is a good choice for people who want style and oil tanned materials are best if you want water resistance.


Another consideration is the rubber outsole. A quality chukka boot should have a durable, slip-resistant sole that is attached to the upper with Goodyear Welt construction or another type of high-quality stitching that ensures it won’t come apart after being worn for several months.

The workmanship on cheaper shoes can be shoddy, so watch out for uneven stitches and glue stains where water seepage may occur in low-end models. If you are interested in buying handcrafted boots from reputable manufacturers, check out Wesco Boots which uses the Blake/Rapid construction method instead of the regular stitch down technique. The Rapid Stitch machine makes welting 25% faster than traditional methods while also providing greater control over material thickness distribution around areas like the tongue and vamp.

Quality boots will have a welt made from the same piece of rubber as the outsole, so you can walk through puddles without worrying about water seeping into your shoes. The only exception to this rule is if it’s intentionally designed that way – such as with Chippewa Water-Resistant Boots which use an all-synthetic upper combined with TPU heel cup and polyurethane midsole – but these kinds of designs are somewhat rare for men’s casual footwear because they lack support compared to traditional welted construction methods (although companies like Timberland do make some models like Euro Hiker). If you want something more stylish than work boots but don’t want to sacrifice durability, waterproof chukkas with a leather upper and rubber outsole are the way to go.


Size is really important because chukka boots are available in so many different width fittings. For example, you can get chukka boots in D, E, and EE widths. So if your feet are on the wider side then you will want to go for a boot that has an “E” or even bigger width fitting.

The best way to measure your feet is by standing with them against a wall. Then place another object (like a book) between both of your longest toes and measure from the top of this object down to the floor along with that inner edge of each foot – just where it meets the wall.

Another way to measure your foot is to place it against a ruler with the heel placed right up at the back. This will give you your length measurement in inches or centimeters. You can then use this information when choosing which size chukka boot would suit you best however always double-check before buying as sizes do vary by brand and even between styles within each collection – don’t rely on them being consistent!

When trying boots on, make sure that you wear the same socks (if any) that you plan to wear once they are purchased. I’d also recommend wearing either flat shoes or trainers under jeans because if there is only one thing worse than an ill-fitting pair of chukkas then it’s having cold feet!

You should also bear in mind that leather boots can stretch slightly. Although, this would be very minimal and is unlikely to make any real difference to the fit of your boot – especially if you are buying a fitted style. So, don’t buy them too small because they will just end up being an uncomfortable pair of shoes instead!

If you buy boots online then it is a good idea to check the return policy. That way, if they don’t fit you can just send them back for an exchange or refund without any hassle.

Size may vary depending on the manufacturer or style. For example, boots from Clark’s menswear tend to fit bigger than those from Converse.

Size tables are available on the brand’s web pages.

The best way to get a true idea of what size would be right for you is by going into a shop and trying them on! However, if there aren’t any stockists nearby then just measure your feet as described above and head over to Google – I assure you that you won’t regret it!

Sizing is important, make sure you understand what size fits your feet best!

Country of Origin

The next important thing you need to know about chukkas boots is the country of origin. This will not only give you an idea of what other people are saying or feeling, but it can also help in deciding if they already have a good reputation around the world. One thing that has been noted with some brands is their location which makes them prestigious and famous because of their superiority over others.

For example, some were manufactured in France. There is an old saying that if you want to manufacture the best products then they should come from Europe, particularly France. You can expect them to be sturdy and durable which makes them perfect for outdoor activities like hiking or camping trips.

There are also other brands made in China where durability was not even considered when they manufactured these chukka boots so better pick up ones with good reviews instead of getting disappointed later on because your money went straight down the drain.

On the flip side, you need to inspect the label before making any purchase decision especially if it only has “Made in Italy” written on its side; this will give you a general idea about their reputation which still needs confirmation through online research.

Boots that are made in the USA are also the same as in Italy because they are considered one of the best in manufacturing chukka boots.

Germany is also one of the countries that manufacture chukka boots which are often made with high-quality materials and excellent stitching.

However, if you want to be sure about their origin then try asking more questions before purchasing them, or better yet visit a shop where there’s someone who can give you an accurate answer that will satisfy your curiosity and needs at the same time.

You can also check out the materials used in making these shoes to ensure that they are of high quality before you make your purchase. The most common one is leather because it’s long-lasting, but some use synthetic material instead which has even better qualities than genuine ones like being more resistant against water and other elements.


Another huge feature of the leather chukka is in its design. They can come in a variety of colors and designs with many different types of detailing on the upper to make them even more stylish. These boots are great for pairing with any outfit and can be worn in both casual and formal situations. Some of the designs available include:

  • Leather chukkas come in a variety of colors such as black, brown, tan, etc. Many also come in two-tone color combinations like dark brown and light brown or white stitching on top of solid darker color leathers.
  • Waterproof chukka boot that has special detailing along the sides and back part of the shoe which is made using suede material to help repel water from getting into your shoes. They also may use other types of materials throughout design such as smooth nubuck or waxy leathers depending on what you choose.
  • Waterproof chukka boots that have a lace-up closure on the top part of the shoe with metal eyelets to help keep your feet secure in place while also looking stylish. This type of boot can come with or without laces depending on preference.
  • Waterproof chukka boots that have a zipper closure on top of the shoe to make putting them on and taking them off super easy. This type is great for people who want an easier time getting into their shoes without having to tie and untie laces every day.

Design is important because it adds a level of uniqueness to the product. Many people are drawn to leather chukka boots because they have that classic rugged look that can be worn in many different settings. It’s not just about being stylish for casual wear, but it is also about comfortability and ease of use which means you’ll want something with more flexibility rather than having to worry about laces every day.


Laces are the most important part of the boot and should be replaced immediately if they start to look worn. This is one area where we recommend spending a little extra money for quality, as cheaper laces will not hold up over time and may fail at an inconvenient moment.

The first decision you need to make when buying your waterproof chukka boots is what type of laces you want. There are two types: round and flat, also known as oval or ribbon.

Round Lace vs Flat – Round laces come in a variety of thicknesses from very thin to quite thick (and yes, there can be a noticeable difference between these). Thinner laces will give you a rounder, more elegant look. Thicker round laces are better for casual boots or situations where you need extra durability (e.g., mucking out stalls). Ribbon-type laces come in a variety of thicknesses as well and will give your shoes a flat profile with clean lines – many people like this aesthetic on dressier shoes such as chukka boots.

The thickness of your round laces will impact how tight or loose a pattern you can form with them; thin rounds tend to be easier to work into more intricate patterns but thicker ones require less effort to create larger, simpler designs. 

The thicker ribbon is harder to use for complex patterns because it’s so stiff – however, this stiffness has an advantage in that it provides superior support at high tension making ribbons better suited for boots where you need extra durability (e.g., mucking out stalls). In addition, while thinner ribbon looks great on casual chukka boots, its lack of stiffness makes it liable to flop around and look sloppy on dressier boots.

The lacing pattern (or lack thereof) is the second thing you should consider when buying your waterproof chukka boots because this will affect how well they fit throughout the day as well as their aesthetic appeal. Traditional patterns consist of three or four parallel lines that run from top to bottom; however, there are many other options available for those looking for something different including crisscrosses, zig-zags, and the Irish Heel/Toe technique which gives a unique diamond shape between each eyelet. 

No matter what type of boot you’re wearing, be sure to avoid both symmetrical designs with equal spacing between all the eyelets and purely random patterns because neither of these will provide a good fit.


Are chukka boots comfortable?

Yes. Chukka boots are comfortable as long as they have been broken in properly and if you buy a pair that is made from high-quality leather.

Are chukka boots still in style?

Yes. Chukka boots are still in style because people can wear them with just about anything, including jeans and khakis.

How do I clean chukka boots?

You will need the following supplies to clean your chukka boots: water, leather cleaner (such as Lexol), a soft-bristled brush or toothbrush, and a soft cloth.

Can I wear chukka boots in summer?

Yes. Chukka boots are very versatile and you can wear them in the summer if they have been made from breathable material such as mesh, nubuck, or leather.

Why is it called a chukka?

There are many theories about why a chukka boot is called a chukka, including:

  • A British polo term that refers to the time between when one player on a team scores and another.
  • Named after Chuka County in Kenya where English soldiers played polo while wearing boots similar to today’s chukkas.
  • Named after a British officer by the name of Chukker who designed them.

Useful Video: 10 Best Men’s Chukka Boots (Part 01) – Men’s Fashion

Final thoughts

Waterproof Chukka Boots are a stylish choice for men. They are a great investment that will last you through the years and can be used in any type of weather or condition.

There’s no need to give up on your favorite pair of shoes just because it is raining outside, so do some research before heading out today! Look at different boots from these brands as well as others, and see what will work best for your needs.

I hope you enjoyed reading and found this Ultimate Guide to Waterproof Chukka Boots helpful!

Good luck!