Last Updated: March 3, 2022

Panama Jack Vs. Timberland: Best Boots For You

Want to get new boots but not sure if you should pick up Panama Jacks or Timberlands? I can help you decide – I’ll tell you everything you need to know about these two brands in this detailed review!

Plus, I’ll also show you some of the best options both from Timberland and Panama Jack, to make it even easier for you to decide!

First, I’ll tell you about the basic features of boots from both brands, which should help you figure out how boots from both brands perform.

And then we’ll compare similar styles from both Timberland and Panama Jack, to see which boots win when we put them head to head!


Best Panama Jack Men’s

Panama Jack Men's Combat Boots, Brown Bark, 10

Best Panama Jack Women’s

Panama Jack Women's High Boots, Brown Cuero B20, 6 us

Best Timberland Men’s

Timberland Men's 6 inch Premium Waterproof Boot, Rust Nubuck, 13

Best Timberland Women’s

Timberland Women's Courmayeur Valley Chelsea Boot, Taupe Nubuck, 085 Medium US

In-Depth Comparison Of Basic Features

In this section, I’ll tell you the most important things about the overall construction and performance of boots from both brands.

One thing to keep in mind is that Timberland gives you a lot more information about their boots than Panama Jack. So if I focus a little too much on Timberland here, it’s simply because they actually wanted to share what goes in their boots.

Warmth And Insulation

Panama Jack boots rarely feature proper insulation. Instead, they have a soft and thick sheepskin lining, which does a great job at keeping your feet warm even in sub-zero temperatures. This is especially useful for women’s boots – it allows you to wear them with just a pair of thighs without having to worry about being cold.

But obviously, not all of the boots are lined with sheepskin. Instead, some have leather or textile lining, which is not really that great at retaining body heat. In those cases, the warmth of the boots usually comes from the thick exterior materials and seam-sealed construction.

What about the Timberlands? Well, in some boots you will have PrimaLoft insulation – one of the best synthetic insulations on the market. It basically replicates the structure of down, so it is able to trap heat inside the boot. But, one area where PrimaLoft is a lot better than natural down is performance in wet weather.

Natural down gets clumpy when wet and then it can’t really trap your body heat. But synthetic insulations, PrimaLoft included, don’t have this issue, and they are able to keep you warm even when you’re stepping in knee-deep snow.

Another thing to keep in mind is that PrimaLoft is really breathable – it allows moisture to pass from the boot so that your feet don’t get clammy or cold. So, whenever you see that a Timberland boot features PrimaLoft insulation, expect superb breathability and warmth.

But obviously, not all of their boots are insulated like this. In those cases, it’s the lining that keeps you warm – usually, it is a thin layer of wool/cotton, and it performs really well.


Breathability is a bit of an issue with Panama Jack boots. Most of them are lined with sheepskin, which is not really a breathable material. Sure, it will keep you warm, but there’s not really a way to air out the boots. And the moisture can’t really escape, meaning that there’s a good chance your feet will get clammy.

Now, this is true for all but one pair of boots in this review, I think. I will show you a pair of boots that has a Gore-Tex membrane. And since Gore-Tex is one of the best performing breathable membranes on the market, you don’t have to worry about breathability at all with that pair.

Timberlands don’t really advertise any particular breathable technology, and yet I’ve found all of them to excel in this area. I’ve never felt hot or too sweaty in any of my Timberlands, so I would definitely recommend them if you’re looking for breathable boots.

Well, they do use a breathable material on the insoles, so I’m guessing that plays a big part. But I will tell you more about that later – for now, I’m focusing on the upper materials of the boots.

And in their classic boots, the breathability comes from the PrimaLoft insulation. It is able to retain warmth and maintain loft at the same time, and that’s why you will feel warm but never too warm in the boots.


All Panama Jack boots in this review are waterproof. They are constructed with leather that is made waterproof, so you have nothing to worry about there. I would still recommend using an impregnation spray on the boots, simply because it provides added protection against dirt and stains.

Oh and there’s also that one pair of boots in this review actually has a Gore-Tex membrane – a waterproof and breathable membrane that performs exceptionally well. And that’s one area where Panama Jack has the upper hand over Timberland.

Most of the Timberland boots features in this review are waterproof. And the ones that aren’t 100% waterproof can easily be made so with an impregnation spray.

The ones that are completely waterproof use leather that acquired those properties during the tanning process. All boots are also either seam-sealed or have an internal waterproof membrane that keeps your feet dry. Actually, one pair of men’s boots has the latter – Timber-Dry Waterproof Technology.

That’s a waterproof lining made from 50% recycled PET (plastic water bottles), and it does an awesome job at not letting any water get inside the boot, but also allowing moisture from the inside to exit.

Grip And Traction

With winter boots, grip and traction are super important, since you’re often walking on really slippery surfaces. And all of that depends on the outsole of the boot – what is it made from, and how flexible is it?

With Timberlands, you’ll see two types of outsoles here. Usually, it’s their classic rubber outsole that you see on most boots:

Timberland Outsole Courmayer Valley

Timberland Rubber Outsole

Panama Jack Rubber Outsole

Panama Jack Rubber Outsole

It’s pretty standard and it performs really well. The lugs are pretty deep, so you have good traction on most surfaces. And it is flexible – the boots are able to bend along with your feet, which gives you a great grip.

One thing that’s interesting is that Panama Jacks have the exact same outsole, just with different branding. Both are rubber, so there’s really no point in comparing them. You can expect great performance in this aspect from both brands. Well, except on ice – in my experience, Timberlands are still really slippery on frozen ground.  

There is one difference though; some Timberlands will also have a midsole, which significantly improves the cushioning and amount of support you get. But none of the Panama Jacks featured in this review have a midsole, so keep that in mind.  

The other type of Timberland outsole you will see here is the L7 Traction Lug Outsole. It is used in their boots that are sportier and in which you actually need really good traction.

The height and spacing of the lugs on this type of outsole are designed to provide you with excellent traction and abrasion resistance on nearly all surfaces. I’d say that they are still not the perfect option for ice, but definitely a better choice than the regular Timberland outsole.

Oh, and with one pair of boots, you’ll see the B.S.F.P. Motion Efficiency System. It’s a technology that allows the outsole to bend along with your foot and allows for ultimate flexibility. But I’ll tell you more about it in the actual boot review!

Insole And Comfort

With Panama Jack boots, you will usually get a removable footbed. And that is perfect for all of you who need to wear a specific type of footbed.

But what about the one inside the boot? Well, it is soft and comfortable. Sometimes it is lined with sheepskin, so it will do a great job at keeping you warm. However, that also means it’s not the most breathable insole.

Additionally, Panama Jack tells you that their insoles are removable for “better hygiene and fit”. Now, I don’t know about you, but that’s not really what I want to hear when I’m buying a pair of $200 boots. What’s wrong with hygiene with your insoles Panama Jack?

Oh right, it’s probably that the sheepskin gets you all sweaty and smelly, and then you can’t do anything about it because you can’t just throw them in the washer.

Keep in mind that that’s not the case with every single boot. Some of them have anatomically formed insoles for superb hygiene and fit – you just have to know what you’re looking for. Remember to check to tables, to see which insoles the boots you’re eyeing have.

We will see one proprietary insole from Timberland – the Ortholite. It is not featured in all of the boots I’ll show you in this review, so keep an eye out for the insole properties in the table.

Timberland Ortholite

The Ortholite is a foam insole that is incredibly comfortable. Whenever you take a step your foot sinks a little into the insole and it provides you with amazing cushioning. That also helps with arch and heel support. Keep in mind that the insole is not removable, so if you need to wear a specific type of footbed, Timberland’s with Ortholite might be the best choice for you.

But maybe you should give them a try – I’ve found that their footbed is so comfortable that I didn’t want to remove it anyway. Additionally, it is made from a breathable and anti-microbial material, so it should not retain any nasty smells.

And if you are worried more about support than cushioning, pick up a pair of Timberlands that have Anti-Fatigue Technology. It is built into the midsole of some boots, and it is great for people who spend most of their days on their feet. It uses geometric cone support to provide you with superb shock absorption and great standing comfort, so your feet don’t get tired too quickly.  


So, neither of these brands is exactly cheap. But they’re also not ridiculously expensive – I’d say they are both mid-range, price-wise.

But if you’re wondering which one has lower prices, I would say that’s Timberland. Most of their boots are in the $100-200 range, and there are very few pairs that go over the higher threshold.

Panama Jack boots are in a similar price range, but there are more pairs that are $200 or up. Now, keep in mind that the price usually depends on the size and color you are getting if you are shopping on Amazon. Which you should be doing by the way, since the boots are much cheaper there than at official retailers!

Panama Jack Vs. Timberland: Women’s Boots

Timberland Courmayer Valley Chelsea Boots Vs. Panama Jack Brigitte Igloo




  Timberland Women's Courmayeur Valley Chelsea Boot, Taupe Nubuck, 085 Medium US Panama Jack Brigitte Igloo
Weight 15.1 ounces / 428 grams (single boot) Not specified
Heel Height 1.75 inches 1.18 inches


Wool/Cotton lining Natural fur lining
Upper Material Nubuck leather Nubuck leather
Outsole Rubber outsole Rubber outsole
Insole Timberland Ortholite insole Removable natural fur lined insole

Since it’s only fair to compare similar types of boots, here we have two Chelsea boots. Both actually look really similar, but there are some notable differences. They are also mostly made from the same materials – the upper is nubuck leather with stretch side panels that allow you to take them on and off in one swift move.

The first one is the height of the boot. The Timberlands are actually taller, and I think that’s an advantage. This makes them warmer in really cold weather and makes them a bit better for snow. But obviously, neither of these is ideal for deep snow – they are pretty short and loose around your ankles.

Because of that, if you step in the snow and your boots fall in it completely, you’ll wind up with snow inside your boots and you don’t want that. But that will happen less often with the Timberlands since they are taller.

The outsole on these is nearly identical, so I don’t think there’s a lot to say about that. I mean the only difference is that the Panama Jacks have an additional lug on the heel – everything else, including the performance, is exactly the same. That also means that both of these don’t perform exceptionally well on ice, so keep that in mind.

Timberland Outsole Courmayer Valley

Timberland Courmayer Valley Outsole

Panama Jack Brigitte Igloo Outsole

Panama Jack Brigitte Igloo Outsole

But there is a catch – the Timberlands actually have a midsole, and the Panama Jacks don’t. And the EVA midsoles on these Chelsea boots really help with cushioning stability, so that’s another advantage of the Courmayer Valley.

The Panama Jacks are lined with natural fur, while the Timberlands are lined with a mixture of wool/cotton. Natural fur is actually the warmer option, but it’s also less breathable. So I think that’s a tie.

The insoles, however, pull in another point for the Timberland boots. They feature Ortholite insoles, which are extremely comfortable, breathable, and provide you with lots of support. The Panama Jack boots, on the other hand, have removable insoles lined with natural fur – not the most breathable or supportive option.

Winner: Timberland Courmayer Valley Chelsea Boot

Timberland 6-Inch Boot Vs. Panama Jack 03




  Timberland Women's 6' Premium Waterproof Boot, Wheat Nubuck, 8.5 M US Panama Jack Womens 03 Boots
Weight 1.25 lbs / 581 grams (single boot) Not specified
Heel Height 1.18 inches Not specified


200 grams of PrimaLoft Leather lining
Upper Material Premium waterproof leather Waterproof Nappa leather
Outsole Rubber outsole Rubber outsole
Insole Removable footbed Removable anatomical footbed


The Panama Jack 03 boots are just as iconic as the Timberland 6-inch boots. Both are warm, waterproof ankle boots meant for more rugged adventures. They both perform really well in snow and wet weather since they are fully waterproof.

With both the Timberlands and the Panama Jacks the upper leather was made waterproof during the tanning process. And they both have nearly identical outsoles, with the same number of lugs:

Timberland 6 Inch Boots Outsole

Timberland 6-Inch Outsole

Panama Jack 03 Outsole

Panama Jack 03 Outsole

If they didn’t have logos, it would be really hard to tell which is which. But when you look at the features, you start to notice some differences – the Timberland boots feature 200 grams of PrimaLoft Eco insulation, which is how they manage to keep you warm. The Panama Jack boots, on the other hand, don’t really have any insulation. And that’s one thing I’m not a fan of – if you want the insulated option of these boots, you’ll need to pay more money.

In terms of support and comfort, I think you’ll find that the Timberlands perform better there. That’s mostly due to their anti-fatigue midsole, which really helps keep you comfortable even after standing for several hours.

The Panama Jacks have a better insole – it is anatomical, so it provides you with better support. But it is removable on both pairs.

This is a really close one. But there is one thing that makes the Timberlands the clear winner here, and it is the fact that they are fully sewn together.

The Panama Jack outsoles are glued to the boots and I really don’t like that. Especially if you are going to wear them all the time and step in snow and puddles – it’s just a matter of time until that glue malfunctions.

Winner: Timberland 6-Inch Boot

Timberland Haven Point Vs. Panama Jack Bambina Igloo




  Timberland Women's Haven Point Waterproof Boot Snow, Black Full Grain, 7.5 M US Panama Jack Bambina Igloo


400 grams of insulation Sheepskin lining
Upper Material Waterproof leather Waterproof Nappa leather
Outsole L7 rubber lug outsole Rubber outsole
Insole Ortholite footbed Removable insole lined with sheepskin


Both of these are tall, waterproof leather boots. But they are pretty different – the Timberland boots are a great choice if you want something comfortable and rugged for hikes or just chilling in the mountains. They are insulated and feature Timber-Dry membrane – a technology that keeps your feet dry in all weather conditions.

The Panama Jack boots, on the other hand, are a great option if you want everyday boots. They are completely lined with sheepskin, so they are really warm. And they are waterproof, so you can safely wear them in deep snow.

And the outsoles confirm this:

Timberland Women's Haven Point Waterproof Boot Snow, Black Full Grain, 7.5 M US

Timberland Haven Point Outsole

Panama Jack Bambina Igloo Outsole

Panama Jack Bambina Igloo Outsole

The Timberland boots feature an L7 traction lug outsole, with Sensorflex Comfort System. It is designed to make the outsole flex along with your foot, providing all the traction and stability you could ever need on uneven surfaces.

The outsole on the Panama Jack boots is pretty basic – a classic rubber outsole with multiple lugs. It performs well on everything except pure ice, so keep that in mind.

The insoles are also pretty different – Panama Jacks have a removable insole, which is lined with sheepskin. It is soft and comfortable, but not really too breathable. The Timberland boots feature the Ortholite foam insole. It is made from an anti-microbial material and has great cushioning.

Overall, I think that this is the least fair comparison since the Timberlands are clearly designed for more rugged adventures. But they also claim that the boots are totally cute and great for everyday, and I don’t agree there. Yes, they’re amazing for uphill hiked in knee-deep snow, but I would pick the Panama Jacks over them to wear with skirts and dresses.  

Best For Hiking: Timberland Haven Point

Best For Everyday: Panama Jack Bambina Igloo

Panama Jack Vs. Timberland: Men’s Boots

Timberland Mt. Maddsen Vs. Panama Jack Bradley C5




  Timberland Men's Anti-Fatigue Hiking Waterproof Leather Mt. Maddsen Boot, Brown, 14 Wide Panama Jack Bradley C5
Weight 1.06 lbs Not specified
Heel Height 1.5 inches 1.18 inches


None None
Upper Material Full-grain waterproof leather Waterproof nubuck leather
Outsole Rubber lug outsole Rubber lug outsole
Insole Foam insole Anatomical insole


So, neither of these boots are exactly winter boots. Both are designed for hiking, mountain climbing, and similar outdoor adventures. So if that’s what you were hoping to find, then you’re in luck!

Both are completely waterproof boots with leather uppers. But the Mt. Maddsen boots also feature Timberland’s proprietary Timber-Dry technology, which acts as a waterproof membrane. It doesn’t allow any water from the outside to enter the boot, but at the same time, it lets moisture from the inside out.

The outsoles are really different on these boots:

Timberland Mt Maddsen Outsole

Timberland Mt. Maddsen Outsole

Panama Jack Bradley C5 Outsole

Panama Jack Bradley C5 Outsole

The Panama Jacks feature the exact same outsole we saw on all of the women’s boots – a classic rubber lug outsole that performs well everywhere except on ice.

The Timberlands perform better in this aspect – they also have a rubber outsole, but the lugs are positioned so that it can bend along with your foot. Timberland calls this B.S.F.P. Motion Efficiency System, which offers improved performance and traction on all surfaces.

The Bradley C5 boots actually have a better insole – it is an anatomical one, and it will provide you with lots of heel and arch support. With the Timberland boots, we don’t really know much about the insole. But that’s because they focused most of their efforts on making a really good midsole.

And they managed to do that – it uses their anti-fatigue technology, which is able to keep you comfortable even after walking or standing for several hours.

The Panama Jack boots are the option that looks better, there’s no denying that. But if you want the boots that perform better at a lower price tag, then you should pick up the Timberlands.

Winner: Timberland Mt. Maddsen

Timberland 6-Inch Boots Vs. Panama Jack 03 Boots




  Timberland Men's 6 inch Premium Waterproof Boot, Rust Nubuck, 13 Panama Jack Men's 03
Weight 1.8 lbs Not specified
Heel Height Not specified Not specified


400 grams of PrimaLoft Leather lining
Upper Material Premium leather uppers Waterproof Nappa Leather
Outsole Rubber lug outsole Gum rubber outsole
Insole Foam insole Anatomical removable insole


We’re comparing the classics again, but this time it’s the men’s options!

So, both of these ankle boots feature waterproof leather uppers. The Panama Jacks feature leather lining on the inside, for improved warmth and water resistance.

The Timberland boots have 400 grams of PrimaLoft insulation, which is actually double the number of women’s boots. It is warm, breathable, and completely waterproof, and it gives these boots an edge over the Panama Jacks.

These two ankle boots have nearly identical outsoles:

Timberland 6-Inch Outsole

Timberland 6-Inch Outsole

Panama Jack 03 Outsole

Panama Jack 03 Outsole

One thing that’s interesting and that I haven’t mentioned before is that the Timberland boots have tiny holes in the outsoles. These allow the boots to breathe so that you don’t get too hot or sweaty in them. At the same time they don’t let any water in – I actually only noticed these on my boots 2 days ago, and I’ve owned them for years!

The outsoles of the Panama Jacks are almost the same – the only thing they are missing are these little holes. Everything else is the same, down to the number and position of the lugs.

The Panama Jacks have a better insole since it is both anatomical and removable. It should give you better support than the one in the Timberland boots, right?

But the Timberlands actually have an advantage here, because of their midsole. It features the anti-fatigue technology I mentioned earlier, which improves the stability and shock absorption of the boots, and manages to keep you comfortable even after you spend hours on your feet.

Winner: Timberland 6-Inch Boots

Panama Jack Amur Gore-Tex Vs. Timberland Earthkeeper




  Timberland Men's Earthkeepers 6' Lace-Up Boot, Medium Brown, 9 M US Panama Jack Amur Gore-Tex
Weight 1.19 lbs Not specified
Heel Height 1 inch Not specified


None Gore-Tex lining
Upper Material Full-grain leather Waterproof greased Nappa leather
Outsole Rubber outsole Rubber outsole
Insole Removable anti-fatigue footbed Anatomical removable insole


The Earthkepeer boots aren’t actually waterproof – you will need to use an impregnation spray on them to be able to wear them in wet weather. But the Panama Jacks are, so that’s one point in their favor. Also, both of these boots feature seam-sealed construction; a really important detail if you plan to wear these on a daily basis.

The Panama Jack boots actually have a Gore-Tex membrane, and that puts them miles ahead of the Timberland boots. Gore-Tex is a high-quality material that makes clothing and footwear waterproof and breathable while being really lightweight at the same time.

The outsoles of the boots are really similar – the Timberlands have a few more lugs for slightly better traction on slippery surfaces. But the difference in performance is really not too noticeable.

Timberland Men's Earthkeepers 6' Lace-Up Boot, Medium Brown, 9 M US

Timberland Earthkeeper Outsole

Panama Jack Amur Gore-Tex Outsole

Panama Jack Amur Gore-Tex Outsole

The insole of the Panama Jack boots is anatomical and removable. The Timberland boots, on the other hand, feature an anti-fatigue insole, which is supposed to provide you with improved stability and standing comfort. And it is also removable, so feel free to replace it with your preferred footbed.

These boots are not insulated, so I don’t think they are the best option for extremely cold weather or really deep snow. These are everyday boots, ones that you can wear to the office and gets loads of compliments.

Since they actually look really similar, I can’t really say that one pair looks better than the other. But I can tell you that the Amur Gore-Tex boots definitely perform better than the Timberlands, in both wet and dry weather.

Winner: Panama Jack Amur Gore-Tex

Panama Jack Vs. Timberland: Our Top Choices

Overall, I think Timberland is the better choice out of the two. Their boots just have more innovative features and are better designed to really get you through the rugged winters.

But that’s not to say that Panama Jacks aren’t any good – they are, but just for different purposes. Panama Jacks are the better option if you want a casual boot that’s beautiful and luxurious.

So, what are your top options from these brands?

For men, I would recommend the Panama Jack Amur Gore-Tex boots regardless of what you are looking for. They are my overall favorite because they are equipped to deal with pretty much everything.

The Gore-Tex membrane makes them completely waterproof and really breathable, and there’s no doubt your feet will be warm and dry all the time in them. But they are not the best choice for snow and really cold weather, because they are not really insulated.

If that’s what you’re looking for, then I recommend the Timberland 6-Inch boots. With 400 grams of PrimaLoft insulation, you’re guaranteed to be warm no matter how cold it gets outside. They are also completely waterproof and really breathable, so really one of your best choices for dealing with snow.

Especially because you will have great grip and traction on nearly all surfaces, except on pure ice.

Timberland Women's 6" Premium Waterproof Boot, Wheat Nubuck, 8.5 M US
  • Classic boot in waterproof leather featuring lace-up front with rustproof hexagonal eyelets and heavily-padded collar
  • Logo embossed at side heel

And for the ladies, I definitely recommend the Courmayer Valley Chelsea boots from Timberland. They are stylish, waterproof, and really comfortable to wear – the Ortholite insoles will help you stay comfortable in these boots even after you spend hours in them.

The outsole will give you plenty of grip and traction, as long as you remember to avoid the icy spots. And the wool and cotton lining on the inside will keep you warm regardless of the temperature while allowing your feet to breathe at the same time. 

Timberland Women's Courmayeur Valley Chelsea Boot, Taupe Nubuck, 085 Medium US
  • Upper made with premium leather from an LWG Silver-rated tannery
  • Herringbone lining

My second choice would be the Bambina Igloo boots from Panama JackDefinitely pick these up if you’re looking for stylish tall boots. They will go great with almost everything you have in your closet.

Because of that, they’re perfect as your everyday boots – stylish enough that you can wear them on a Friday night, but warm and comfortable enough that you don’t have to be afraid of knee-deep snow. That’s because they are also waterproof and fully lined with sheepskin. 

Those are my top picks for you. But you’re fine even if you like some other pair of boots – all of the ones I showed you here have great reviews and are worn and loved by lots of people. Head over to Amazon to see this for yourself, and check out the prices and color options of the boots!

And if you didn’t see anything you liked here, check out our other reviews – maybe you’ll find your new boots there. 


About the Author Roger Timbrook

Roger is a little obsessed with travel. He has been to over 40 countries, broken 3 suitcases and owned over 10 backpacks in 12 months. What he doesn't know about travel, ain't worth knowing!

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