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Timberland Chillberg Insulated Review

A highly functional winter insulated boot that also looks nice
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Timberland Chillberg Insulated Review
Credit: Timberland
Price:  $150 List
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Manufacturer:   Timberland
By Andy Wellman ⋅ Senior Review Editor  ⋅  Nov 4, 2020
  • Warmth - 25% 7.0
  • Water Resistance - 25% 7.0
  • Fit and Comfort - 25% 6.0
  • Ease of Use - 15% 7.0
  • Traction - 10% 8.0

Our Verdict

The Timberland Chillberg Insulated does everything you need of a boot (namely keep your feet warm, dry, and comfortable), all while looking a lot nicer and more interesting than most of the competition. While looks may not be the most important consideration for tromping around in the woods on a winter hike, it matters to a lot of people who need winter boots during their day-to-day lives. Coming in two color options — “Wheat” or Black — these boots look as nice as they wear. We think they are a solid choice for anyone who likes a looser fitting boot and found that they perform well for everything from winter chores to walking through town, and can even handle some miles in the woods if need be.
Loose and comfortable fit
Waterproof to six inch depth
Wide fit in heel and ankle cuff
Lacing hard to dial in just right
Fleece lining pills up

Our Analysis and Test Results

The Chillberg looks a whole lot like you might expect of a boot made by Timberland but has the bonus of including Primaloft insulation and a coated waterproof leather outer in its design. We like how they look like a normal work boot, not simply like an oversized and overstuffed hiking boot, which has limited off-trail appeal. Initially, they struck us as being oversized and a bit clunky when walking about, but over time we really came to appreciate the loose fit that is comfortable but not imprecise. The fully threaded lacing system uses a combination of d-rings and metal grommets, and while it doesn't easily cinch down to make the fit of the boot tighter, we came to understand that these boots are simply more comfortable if you leave the fit slightly loose. The boot comes with an insole that is a bit flimsy and rather unremarkable; it doesn't have reflective materials or extra insulation like some found in other boots. That said, it is easily replaceable if you feel the need. We also commend Timberland for using a fair amount of recycled materials in the construction, which features both inner fleece lining made of recycled plastic bottles as well as 34% recycled rubber for the outsole.

Performance Comparison

timberland chillberg insulated - the chillberg are our favorite winter boot for wearing around town...
The Chillberg are our favorite winter boot for wearing around town because they look a lot nicer than most we have tested, while also providing impressive warmth, plush comfort, and total waterproofness.


The Chillberg adds 400g of Primaloft insulation in a thin layer stuffed inside these boots. We were initially quite impressed by how thin the insulation felt, comparable to boots with half as much, but eventually just enjoyed that we were wearing a thinner and lighter boot that still kept our feet warm.

Overall, though, these boots were not the best performers in our dedicated warmth test, which involved submerging them in a bath of freezing water and ice for 12 minutes, measuring the drop in internal temperature using a laser thermometer, and comparing them to other boots. In this time, they dropped about 19.2 degrees overall and finished with an interior temperature of 43.8F. While this wasn't the worst performer, it also was nowhere close to the best.

With those results in mind, we didn't expect too much out of our second warmth test, with our foot in the boot. However, we were pleasantly surprised that, overall, our feet stayed quite cozy. We did notice a few cold spots inside the boots, especially on the heel and ankle area where the fit is looser and not as close to the foot, yet also appreciated how we could move our toes around in order to keep them warm and full of circulation.

timberland chillberg insulated - the warmth in the chillberg is provided by 400g primaloft...
The warmth in the Chillberg is provided by 400g Primaloft insulation, which is lined with the soft black and grey felt shown here. We aren't in love with the liner because it pills up, but for such a thinly insulated boot, it sure is warm.
Credit: Andy Wellman

Water Resistance

Made completely of treated leather, with no rubber bathtub above the sole as many winter boots are designed, we also didn't expect complete waterproofness out of this boot. However, we were once again surprised when it passed our water submersion test with flying colors. After standing in roughly five inches of freezing cold water for 10 minutes, there was not a hint of water inside these boots, and the waterproof coating meant that none soaked into the leather exteriors either.

The top of the gusseted tongue would therefore be the lowest part of the boot where water could leak into the inside, and we measured this at six inches above the ground, which was not bad, considering most people do not walk through six-inch deep puddles very often. Over time, we would anticipate that the waterproof coating of the leather will wear off and break down, so you will need to apply an aftermarket treatment to keep these boots from absorbing water as leather tends to do. Timberland sells a spray-on version that they recommend, although we did not test it.

timberland chillberg insulated - performing the water test, in which we stood in this half-frozen...
Performing the water test, in which we stood in this half-frozen lake for over ten minutes to test the waterproofness of these boots. The Chillberg performed great, and also have a decent 5.75 inch flood height.
Credit: Andy Wellman

Fit and Comfort

These boots fit a bit wide and sloppy for a hiking boot, one major reason that we enjoy them much more for use around town, where their loose fit is a major contributor to their comfort, rather than a detraction. While we initially felt the boots were simply too big, we found that wearing a thick sock helps a lot with the extra volume on the inside, and we also notice that the length is spot on for the size, so wouldn't want to size down or we would be risking cramming our toes into a boot too small.

Since they are designed to be loose-fitting, we actually found them to be quite comfortable. This comfort is made even better if you leave the high cuff around the ankle and shin loose, as in, don't pull the laces tight before tying them. We should warn you that if you want this boot but also want a snugger, more precise fit, this is difficult to accomplish since the way the leather is sewn on top of the foot prevents the laces from cinching up very much.

timberland chillberg insulated - the fit on this boot is loose, and you sort of want it that way due...
The fit on this boot is loose, and you sort of want it that way due to the way the tongue is sewn on the top of the boot. It doesn't lend itself to being compressed or bent over if you want to try to tighten the laces down. They are comfortable and loose.

Ease of Use

For a lace-up boot, these are pretty easy to use. They feature flat laces that are threaded through four rungs of d-rings at the bottom and then threaded through two metal lined eyelets higher up on the ankle cuff. If the laces come unthreaded from these eyelets, then it is a bit laborious to rethread them very quickly, but we found that they usually stay in place. Putting the boots on, then, involves simply slipping the foot inside and then tying the laces in place. As opposed to most winter hiking boots that feature laces, we found these boots are most comfortable when you do not cinch them up too tight for a snugger fit.

Keeping in mind the intention for these boots to fit loosely, they are a bit easier to repeatedly put on and take off in short amounts of time than others that require looping the laces through hooks on the upper shaft. That said, they are nowhere near as simple as slip-on boots or even some Pac-boot designs.

timberland chillberg insulated - the lower half of the laces resist tightening due to the shape of...
The lower half of the laces resist tightening due to the shape of the sewn-together leather on the top of the foot. You can crank down the upper two laced eyelets, but we found these boots to be more comfortable if you leave them slightly loose.


We really like the level of traction offered by the Chillberg. Its outsole is made up of 34% recycled rubber, a nice touch, and features a design pattern made up of roughly 5mm deep rectangular lugs well-spaced out on the sole of the boot. There is more negative space than surface area of exposed lugs, which gives them a cleat-like effect, allowing them to more easily punch into hard snow surfaces. The lugs are also flat on top, providing the surface area to grip on non-snowy surfaces like pavement, dirt, or ice.

timberland chillberg insulated - the traction on the bottom of this boot features well-spaced lugs...
The traction on the bottom of this boot features well-spaced lugs that add to their punch as they grip into soft surfaces like snow, or even hard-packed snow.

Over the years, we have found that a lug pattern similar to the Chillberg is the most effective for gripping in surfaces like snow and mud because the pressure is localized into cleats that dig into slippery surfaces better. Many of the top trail running shoes have a similar lug pattern as these do.

timberland chillberg insulated - no boot does especially well gripping on ice, and neither does this...
No boot does especially well gripping on ice, and neither does this one. However, it grips very well on all other surfaces that we tested it on, and with a modified gait, sliding the feet along, we were able to stay on our feet just fine.


These boots rest squarely in the middle of the price range when compared to their competitors. We also found that they are roughly in the middle in terms of performance as well, suggesting that they offer decent value. How valuable they end up being for you likely depends on your intended uses. If you want a good-looking boot for wearing around town when snow covers the ground, these are a good bet.

timberland chillberg insulated - we went on hikes in this boot in cascades of oregon while waiting...
We went on hikes in this boot in Cascades of Oregon while waiting for the snow to fall in November, and felt that they were plenty comfortable, despite their looseness. We think they provide good value, and look nice as well.


The Timberland Chillberg Insulated are worthy of our recommendation based largely on their comfortable and loose fit combined with their more fashionable and appealing design. They stand out in comparison to a genre of boots that either tends to look like giant hiking boots or like small snowboard boots. While they are not the top performer in our overall ratings, they are reasonably warm and totally waterproof to six inches, and also feature great traction. These are a solid and stylish pair of boots.

timberland chillberg insulated - stomping through soda creek in the oregon cascades, something we...
Stomping through Soda Creek in the Oregon Cascades, something we enjoyed doing in the supremely waterproof Timberland Chillberg.
Credit: Andy Wellman

Andy Wellman