8 Best Insulated Chukka Boots for Casual Winter Warmth


When the temperature drops, finding insulated chukka boots for winter can make those brutally cold, snowy days a bit more tolerable. I like the Hush Puppies Men’s Beauceron Insulated Casual Boots because they have a sleek style and use 3M Thinsulate to insulate the boot, which is very good at trapping heat but also lightweight and non-bulky.

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These are my choices for best winter chukka boots:

  1. Hush Puppies Men’s Beauceron Winter Boots (click here to view)
  2. Timberland Men’s Port Union Waterproof Insulated Boots (click here to view)
  3. Lands’ End Men’s All Weather Leather Insulated Winter Boots (click here to view)
  4. Kodiak Men’s Rhode II Arctic Grip Insulated Casual Boots (click here to view)
  5. Hush Puppies Men’s Beauceron Ankle Winter Boots (click here to view)
  6. Giovanco Men’s Warm Plush-Lined Waterproof Ankle Boots (click here to view)
  7. *Sneaker Boot* Sorel Men’s Cheyanne Metro Hi Insulated Sneakers (click here to view)
  8. *Sneaker Boot* Helly Hansen Men’s Bowstring Primaloft Sneakers (click here to view)

To insulate boots, companies will use synthetic insulation that is lightweight and non-bulky, which means it can be used to line the interior of a boot without affecting how the boot fits and looks. The amount of insulation used will vary, and will affect the warmth of the boot.

For casual boots, you will typically see either 200g or 400g of insulation used. The 400g boots will be warmer. While it’s impossible for me to know your weather conditions, in my experience, 200g boots keep my feet warm in typical, moderate winter conditions. For extreme weather, I’m using 400g (or higher).

In this article let’s take a closer look at the best insulated 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 these types of insulated casual boots.

Best Insulated Chukka Boots for Winter

Hush Puppies Men’s Beauceron Winter Boots

These Hush Puppies men’s insulated casual boots are made with waterproof full-grain leather and feature premium Vibram Arctic Grip outsoles designed to help provide needed traction in wet environments. Here’s what you need to know about these boots:

  • Insulation – Yes, these boots are insulated. They use 200g of 3M Thinsulate to insulate the interior of the boot. 3M Thinsulate is a very popular synthetic insulation used in footwear because it is very good at trapping heat, but is also non-bulky and lightweight, so it doesn’t affect the look and fit of the boot.
  • Material – These boot are made using full-grain, waterproof leather. The Vibram Arctic Grip outsoles are made with rubber and designed to provide needed traction in wet conditions.
  • Style – These chukka-style boots have a moc-toe design that fit up near the ankle. Hush Puppies also offers a rounded toe insulated version of this boot. Click here to view this round-toe version available at Amazon (affiliate link takes you to Amazon.com).

Click here to view these Hush Puppies Men’s Beauceron Insulated Chukka Boots available at Amazon (affiliate link takes you to Amazon.com). They have a removable footbed that can be easily swapped and cleaned when needed.


Timberland Men’s Port Union Waterproof Insulated Casual Boots

These Timberland Port Union Waterproof Insulated Casual Boots use PrimaLoft for insulation. PrimaLoft is another popular type of synthetic insulation used in boots that is very good at trapping heat, but also lightweight and non-bulky. Here’s what you need to know about these boots:

  • Insulation – Yes, these boots are insulated. They use 200g of PrimaLoft for insulation. PrimaLoft is a down replacement that isn’t as bulky, but still traps heat. These synthetic insulations are used in footwear because using an insulation like down would make the footwear awkward and bulky.
  • Material – These Timberland boots are made leather uppers and rubber outsoles. They feature a waterproof design that that uses a breathable membrane to help keep moisture out, but still allow your foot to breathe. Rustproof hardware used so water does not affect eyelets and laces.
  • Style – These casual boots have a rounded toe and are designed to fit up over the ankle. They use Timberland’s “Sensorflex” midsole design which helps create extra cushioning under the foot.

Click here to view these Timberland men’s insulated chukka boots available at Timberland (affiliate link takes you to Timberland.com). These are 6-inch boots that will fit up over the ankle.


Lands’ End Men’s All Weather Leather Insulated Winter Boots

These Lands’ End Men’s All Weather Insulated Casual Boots not only use synthetic insulation, but they also have a faux shearling lining around the collar to help trap heat and provide warmth. Here’s what you need to know about these boots:

  • Insulation – Yes, these boots are insulated. They use 200g of Thermolite to insulate the interior of the boot. Although this type of insulation is different than the 3M Thinsulate used in the first boots we discussed, it’s another type of synthetic insulation that is very good at trapping heat, but also non-bulky.
  • Material – These boot are made using leather uppers and rubber outsole that is designed in a way to provide extra traction. As we discussed above, the collar has a faux shearling lining to provide extra warmth around the ankle.
  • Style – These casual boots have a moc-toe design. The rubber outsole wraps up to offer a small bit of protection to the front toe of the boot. They have EVA footbeds to provide cushioning under the foot.

Click here to view these Lands’ End men’s insulated chukka boots (affiliate link takes you to landsend.com). They’re designed to fit up around the ankle and have a pull tab to make it easier to slip the boots on.


Kodiak Men’s Rhode II Arctic Grip Insulated Casual Boots

These Kodiak insulated casual boots actually use 400g of 3M Thinsulate for insulation, so they will provide more warmth than the 200g boots we have listed above. Kodiak comfort rates these boots to -30°C, -22°F. Here’s what you need to know about these boots:

  • Material – These boot are made using waterproof leather that is also designed to resist stains made by salted streets and sidewalks. The Vibram Arctic Grip outsoles are made with rubber and designed to provided needed traction in wet conditions.
  • Insulation – Yes, these boots are insulated. They use 400g of 3M Thinsulate to insulate the interior of the boot. As we discussed earlier, 3M Thinsulate is a very popular synthetic insulation used in footwear because it is very good at trapping heat, but is also non-bulky and lightweight, so it doesn’t affect the look and fit of the boot. Kodiak comfort rates these boots to -30°C, -22°F.
  • Style – These Kodiak insulated casual boots have a round-toe design and fit up near the ankle. They have a trimmed collar for comfort and are made with removable EVA insoles that help absorb shock.

Click here to view these Kodiak men’s insulated chukka boots (affiliate link takes you to Kodiak.com). Again, these boots use more insulation (400g) than some of the other boots on our list, and Kodiak comfort rates these boots to -30°C, -22°F.


Insulation Used in Winter Chukka Boots

As we discussed earlier, companies will use synthetic insulation that is lightweight and non-bulky to insulate boots. This allows them to line the interior of a boot without affecting how the boot fits and looks. The amount of insulation used will vary, and will affect the warmth of the boot.

insulated-chukka-boots

For insulated casual boots, you will typically see either 200g or 400g of insulation used. The 400g boots will be warmer. While it’s impossible for me to know your weather conditions, in my experience, 200g boots keep my feet warm in typical, moderate winter conditions. For extreme weather, I’m using 400g (or higher).

Unfortunately, it is almost impossible to find insulated chukka boots that use more than 400g of insulation. Anything above 400g is typically used for extreme conditions, and can actually cause a boot to be too warm if you’re simply wearing it in moderate winter conditions.

If you want to explore other options, visit our articles linked below about insulated winter boots:


4 Things to Consider When Buying Insulated Chukka Boots

Waterproof Liners

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

  • Does it Have a Liner – Some insulated casual 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 work boots or rubber work boots.

To read more about waterproof chukka boots, visit our article about the best waterproof chukka boots.

Outsole

What type of outsole do you need? Obviously, for wet winter conditions, having an outsole designed to maximize grip is important. For example, the Hush Puppies insulated chukka boots at the top of our list use Vibram Arctic Grip outsoles designed to provide needed traction in wet conditions.

Many regular chukka boots designed for urban settings have soft and flat outsoles, so be sure to consider the amount of grip your boot will provide.

Seam Sealed

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

To waterproof an insulated casual 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 insulated 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).

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

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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