10 Best Waterproof Chukka Boots for Stylish, Dry Comfort


Splish, splash your boots are taking a bath. Perhaps it’s time to turn to waterproof chukka boots. If so, you’ll need to decide whether you want a traditional chukka style, or more of a chukka sneaker-boot. I personally own the Rockport Rugged Bucks Boots below. They have that classic chukka design and, yes, help keep my feet dry.

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These are our choices for best chukka waterproof boots:

  1. Rockport Men’s Rugged Bucks Waterproof Boots (click here to view)
  2. Clarks Men’s Desert Boot GTX Waterproof Chukka (click here to view)
  3. Rocky Men’s Outback Gore-Tex Waterproof Hiker Boots (click here to view)
  4. Sorel Mens Madson Chukka Waterproof Boot (click here to view)
  5. Timberland Mens Kendrick Waterproof Chukka Boots (click here to view)
  6. Sorel Men’s Kezar Chukka Waterproof Boot (click here to view)
  7. Keen Footwear Men’s Glieser Chukka Nylon Waterproof (click here to view)
  8. ECCO Men’s Turn GTX Lace-Up Boot (click here to view)
  9. *Women’s* Timberland Nellie Waterproof Chukka Boots (click here to view)
  10. *Women’s* ECCO Soft 7 Tred Gore-tex High Sneaker (click here to view)

Not all chukka boots are made equal. Some are specifically designed for outdoor environments, while others make more sense in urban settings.

The outsole is a big giveaway. Do you need a deep lug outsole for hiking or other outdoor activities? If so, I’d recommend the Rocky boots on our list.

Some boots (like the Clarks chukka boots) use a crepe outsole that is soft and comfortable, but might make more sense for office and urban settings. There are also some chukka boots (like the Rockport Rugged Bucks Boots) that have a sort of hybrid design that can be used both inside and outside.

In this article let’s take a closer look at the best waterproof chukka boots on this list so you can find an option that works for you. Let’s also discuss a few things you will want to consider when buying waterproof boots.


5 Things to Consider When Buying Waterproof Chukka Boots

Waterproofing

When it comes to waterproof work boots, some companies will use a play-on-words to make you think that you are getting more waterproof protection than you think. Quickly, two things to know:

  • Does it Have a Liner – Some boots may be marketed as “waterproof”, but just simply have waterproof leather and no liner. For better protection, you will want both waterproof leather and a waterproof liner. To read more, visit our article about what makes a boot waterproof.
  • True Waterproof – It is very difficult for a leather work boot to be completely waterproof. Yes, seam sealed leather and a waterproof liner helps, but don’t expect to submerge the boot in water and come out completely dry. For that, you’d need pvc boots or rubber boots.

For other indoor/outdoor options, visit our article about the best composite toe hiker boots. If you are interested in insulated options, visit our article about the best insulated chukka boots.

Gusseted Tongue

Tongue gussets connect the sides of the tongue to the boot which help keep water and other debris out. Not all waterproof chukka boots will have this tongue gusset.

The Rockport Rugged Bucks Boots at the top of our list do have a gusseted tongue.

Outsole

What type of outsole do you need. If you are looking for an outdoor chukka boot, then you’ll likely need an outsole with deep lugs. For more urban settings, outsoles that are soft and flat might add comfort and make more sense.

If you are looking for waterproof boots to use on concrete, I’d highly recommend wedge sole boots for comfort. To read more, visit our article about the best waterproof wedge work boots. For safety toe, visit our article about the best waterproof composite toe boots.

Seam Sealed

Seam sealing is an important step in waterproofing a boot. When a boot is stitched and built, the small needle holes present opportunities for water to get into the boot.

To waterproof a boot, these companies will seal the seams with waterproof taping to help cover these needle holes. Some boots will also seam seal the insole to prevent water from getting in from underneath the foot.

Additional Waterproofing

You can also buy waterproofing spray to apply to your chukka boots over time to help them maintain a superior level of water resistance. Many of these sprays add a silicone protection to the outside of your boot.

If you are interested in waterproofing spray, here is a popular option available at Amazon (affiliate link takes you to Amazon.com).


Best Waterproof Chukka Boots

Rockport Men’s Rugged Bucks Waterproof Boots

I would highly recommend these Rockport chukka boots if you are looking for a comfortable, casual boot that also has water protection built in. Another small thing I have grown to like about these boots, is mine are very quiet and don’t squeak when I walk.

Here’s what these boots look like:

This is the current price of these Rockport chukka waterproof boots available at Amazon (affiliate link takes you to Amazon.com). Here’s what you need to know about these boots:

  • Material – The waterproof leather construction of this boot is both easy to clean and long-wearing.
  • Water Resistance – Rockport’s Hydro-Shield® ensures that feet stay dry with its waterproof leather, a gusseted tongue and an insole that is seam-sealed and waterproof.
  • Comfort – This lightweight boot is flexible with a TPR outsole for superior shock absorbency, which provides traction and aids in the reduction of foot and leg fatigue. The EVA footbed molds to the shape of the foot. Also has padding up around the collar.

Like I said, these are the waterproof chukka boots that I use. I like the way they look and feel. Mine make very little noise when I impact the ground, and are comfortable to wear.

Here’s what mine look like:

waterproof-chukka-boots
Rockport-rugged-bucks-boots-front

These boots have a gusseted tongue and seam-sealed insoles for extra water protection:

Rockport-rugged-bucks-boots-inside
Rockport-rugged-bucks-boots-worn

In my opinion, these boots are very comfortable to wear. The outsole is comfortable and quiet, and the padding around the collar helps too.

Rockport-rugged-bucks-boots-bottom
Rockport-rugged-bucks-boots-worn-front

Click here to buy these Rockport waterproof chukka boots available at Amazon (affiliate link takes you to Amazon.com). These boots have a nice indoor/outdoor design, and fit in both on and off the clock. In my experience, these boots fit true to size.


Clarks Men’s Desert Boot GTX Waterproof Chukka

Clarks desert boots have been a popular chukka boot for years, and they do offer it in a waterproof version. This boot has a Gore-Tex liner to help keep your feet dry in wet conditions.

Here’s what these Clarks GTX Waterproof Chukkas look like:

This is the current price of these Clarks waterproof desert boots available at Amazon (affiliate link takes you to Amazon.com). Here’s what you need to know about these boots:

  • Material – The handsome, premium leather construction of this boot lends it a versatility that can take it from the office to a night out with friends.
  • Water Resistance – The breathable GORE-TEX® membrane delivers superior waterproofing while allowing your foot to breathe for adequate comfort in any climate.
  • Comfort – The crepe rubber sole provides extra traction when you need it. The heel of this boot measures approximately one inch.

Like we discussed earlier in the article, some chukka boots are built more for urban environments. The crepe rubber sole is very comfortable and adds cushioning on hard surfaces like concrete.

Here’s a look at the crepe outsole on my standard Clarks Desert Boots (non-waterproof version):

clarks-desert-boots-outsole

Now, to be clear, the waterproof version of these boots does have a different outsole pattern than the original Clarks Desert Boots I own (photo above). But even though these Clarks chukka boots are inspired by World War I British officer boots, in my opinion, these are best used for office and urban settings. If you are looking for a hiking chukka, I’d choose a boot with deep-lug outsoles (like the Rocky boot we discuss next).

In fairness, crepe soles can do a good job with slip resistance. The rubber base is soft enough to absorb small grit and gravel over time, which can help add traction to the bottom of a boot. But if I’m looking for a hiking boot, I’m personally choosing a deep-lug outsole.

Click here to buy these Clarks GTX waterproof chukka boots available at Amazon (affiliate link takes you to Amazon.com). These jeans are machine washable.


Rocky Men’s Outback Gore-Tex Waterproof Hiker Boots

Rocky Boots is an Ohio-based shoe company that opened in the 1930’s and makes several different types of boots. Rocky makes work boots, outdoor boots, hiking boots, and tactical boots.

If you are looking for chukka boots to use while hiking, these are a great option. Here’s what these boots look like:

This is the current price of these Rocky waterproof hiking chukka boots available at Amazon (affiliate link takes you to Amazon.com). Here’s what you need to know about these jeans:

  • Material – These waterproof moc toe boots features a full-grain leather upper and a fully padded collar for durable all-day comfort.
  • Water Resistance – GORE-TEX® technology makes this boot both windproof and waterproof. The exceptionally breathable lining keeps rain, sleet, and snow out but allows perspiration to evaporate with ease.
  • Comfort – The extra-thick, removable PU Rocky Terra Suspension footbed features Air Flow design for outstanding support and cushioning for remarkable ease of wear. Outback outsoles provide increased stability on rugged terrains.

Click here to buy these Rocky moc-toe chukka boots available at Amazon (affiliate link takes you to Amazon.com). The leather on these boots is designed to feel broken in on the first wear.


Sorel Men’s Kezar Chukka Waterproof Boot

These Sorel boots have a modern sneaker-boot design that can work in both professional and casual environments. Here’s what these Sorel waterproof chukka boots look like:

This is the current price of these Sorel waterproof chukkas available at Amazon (affiliate link takes you to Amazon.com). Here’s what you need to know about these boots:

  • Material – This boot is crafted from rich, full-grain leather that looks good and performs amazingly well.
  • Water Resistance – From the waterproof leather to the combination pigskin/textile lining and seam-sealed construction, you can feel confident taking on a rainy day because you’re staying dry.
  • Comfort – These boots help you stay comfortable with removable, molded EVA footbeds. They have molded rubber outsoles with ground-contact EVA down the center providing superior traction.

Click here to buy these Sorel chukka boots available at Amazon (affiliate link takes you to Amazon.com). These boots have waterproof leather and a seam-sealed construction, but don’t have a waterproof liner.


Other Waterproof Chukka Boots to Consider

  • Timberland Mens Kendrick Waterproof Chukka Boots – These are stylish chukka boots that are perfect for business casual environments. Waterproof, full-grain leather. These boots provide the style and look of dress shoes in a comfortable fit that gives you a classy look that is easy to wear. Click here to view these Timberland boots (affiliate link takes you to timberland.com).
  • Sorel Mens Madson Chukka Waterproof Boot – Another nice option made by Sorel. These boots are seam-sealed and made with waterproof suede uppers. Removable memory-foam insoles provide superior comfort throughout the day. These boots have durable outsoles that can be used both indoor and outdoor. Click here to view these boot at Amazon (affiliate link takes you to Amazon.com).
  • *Women’s* ECCO Soft 7 Tred Gore-tex High Sneaker – Ecco offers several types of waterproof boots, including these women’s waterproof chukkas. These boots have a Gore-Tex waterproof liner. Built with a side zipper for easy on and off, these are sneaker chukkas built for casual use. Click here to view these ECCO women’s waterproof chukka boots (affiliate link takes you to Amazon.com).

***Service boots are another good option to consider when looking for indoor/outdoor boots that can also be worn casually. To read more, visit our article What is a Service Boot?

Paul Johnson

Paul is a lead content creator for Workwear Command. He has had several blue-collar jobs which have provided him a wide range of experience with tools and gear. He also has a business degree and has spent time in business casual office settings.

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