Caterpillar vs Timberland vs Woodland

Caterpillar, Timberland and Woodland all produce shoes and boots of excellent quality, both in materials and construction. So when it comes time to choose, where do you start?

We will cover all three brands, giving you the information you need to answer that question. But the one thing you can count on is that Timberland will have the largest selection.

However, that does not mean you should always necessarily start with Timberland products. Because the smaller selections have some very nice options from which to choose, and it won’t take long to determine if there is anything that works for you.

So, depending on what type of shoe you’re looking for, it might be best to look at what the smaller selections have to offer, then go to Timberlands to see if there is anything you like better. But we will even make that easier, because sometimes it actually is better to go straight to Timberland products, and we’ll tell you when that is the case.

Here is a sampling of what the three brands have to offer in all major categories of shoes and boots.

Men’s Boots

This is the most competitive category amongst the three brands, and it’s the one for which they’re all famous. They each offer very similar styles, including the available color options. Yet…there are some very significant differences.


There is no question that the Caterpillar Second Shift 6 inch plain soft toe boots are handsome, functional footwear. The hex-shaped grommets, dual-colored laces, and speed lacing contribute to a very stylish look, while the textured outsole provides oil-resistant traction.

There is a plush collar for added comfort and a back finger loop for easy on and off. Also, a Climasphere lining wicks moisture and helps to regulate the temperature in order to keep feet cool and prevent blisters. There are also contoured removable insoles. Caterpillar Men’s Second Shift Work Boot are a functional piece of footwear that strongly contribute to Caterpillar as a brand, it shows that they mean business in the shoe market. 

Nothing is sacrificed for comfort and style, though. These boots are engineered with electrical hazard protection and are ANSI approved against open circuits of up to 600 volts in dry conditions. The Honey color is closest to the classic Timberland favorite, Wheat Nubuck, but it is also available in Black and Dark Brown.


The classic Timberland 6 inch steel toe boot is recognizable anywhere, particularly in the popular Wheat coloration. Without the gold-toned grommets and speed laces, the Timberland isn’t quite as eye-catching as the Caterpillar, but that is not as much of a factor in the brown and black models.

A waterproof lace-up leather boot with textured rubber slip- and oil-resistant lug outsoles, this boot has an excellent comfort system that provides arch support and reduces foot fatigue even while toughing out the most rigorous day on a job site. 400 grams of insulation has also been added for extra warmth.  Timberland PRO Men’s Titan 6″ Work Boot are a great addition to the Timberland brand, they’re functional and stylish with the companies signature durability and longevity.  

The padded collar at the top of the boot offers even more comfort, as does the mesh lining that has an anti-microbial treatment for odor control. This rugged boot is a wonderful example of merging form and function…except…there is no speed lacing.

Without speed lacing, you have to loosen the top few eyelets so much that it may be necessary to completely take the laces out in order to remove the boot. That means when it comes time to put them back on you have to rethread the eyelets, which can be a more time-consuming process than a lot of people want to put up with.


There is a 6″ Soft Toe Waterproof Industrial & Construction Work Boot from Woodland that is of a similar design to the Caterpillar and Timberland, offered in Black, Dark Brown, and Brown colors. They feature leather uppers and welted textured soles, just like the other two brands. However, like Timberlands, the Woodland boots don’t have speed lacing. Also, while all of the elements are similar to the other two brands, the boot somehow manages to just fall short in style.

Woodland Men’s Composite Toe Waterproof Work Boots come in as a functional, utility work boot which can compete directly with Timberland.  It doesn’t sacrifice in many areas, although again, the style may not be for everyone.  

Winner: Caterpillar

While style preferences are completely subjective, I happen to think that the Caterpillar has an extra bit of dash. But, completely disregarding that, the speed lacing is enough by itself to make it the winner here. Having to rethread eyelets every time you put your boots back on is just a pain. And, finally, the electric hazard protection tips the decision.

Women’s Shoes

Once again, Timberland outstrips the competition by far in the variety of offerings. However, they are not the only brand with attractive styles.


Surprisingly, Caterpillar not only has some nice boots for women, but their non-boot choices are very attractive, as well. For instance, there are several styles of sandals that are as stunningly fashionable as you’ll find from any other manufacturer.

The Kobbi Gladiator Sandals are both airy and sophisticated. Featuring studded leather straps in leather, a comfy polyurethane insole, and rubber outsole, the Kobbi has a practical and attractive 1.25” heel height.

But Caterpillar’s Jazmyne Dress Sandals, Teshie Flat Sandal, Westwood Wedge Sandal and many more are definitely worth a look. Unfortunately, Caterpillar falls a little flat on shoes that are not boots or sandals. I’m not sure it’s even worth looking if you just need simple flats.


Basically, Timberland has everything except super formal high heels. Whether you need boots, booties, boat shoes, sandals or flats, you can find something truly eye-catching from Timberland.

It’s probably not surprising, though, that one of the finest women’s ankle boots around is Timberland’s feminine take on its classic work boot. The Glancy field Chukka Boot is a high heeled ankle boot with a rubber lug outsole to provide traction and a textured rubber chunky stacked-heel for stability.

The boot features 100% recycled laces and a 50% recycled mesh lining that is breathable and comfortable, in addition to being environmentally conscious. An anti-odor ortholite footbed offers moisture management and breathability for all-day support and comfort.

However, while Timberland certainly excels at boots for both men and women, there is no lack of lovely choices in all other types of shoes.

Winner: Timberland

Chances are you can find more than enough from which to choose at Timberland, regardless of what type of shoes you’re looking for.

Still, if you want cute boots or sandals, it would be worth taking a quick look at Caterpillar products. There are definitely some great offerings to consider there.

If you need rain boots and have a taste for quirky, then you may benefit by a quick look at Woodland. Otherwise, I wouldn’t bother.


This category is so easy it was tempting to not even include it, because Caterpillar and Woodland don’t even have shoes for kids. But to skip it completely would be doing a disservice to kids everywhere, because Timberland has an awesome selection of shoes for kids.

Yes, you can get the classic ankle boot in popular wheat for kids of all ages, including Velcro closures for toddlers. But here are just a few other styles for the little ones and the older set.

For newborns to 8 year olds, you can get a two-piece bootie and striped hat set in wheat, blue, or pink. They come in a gift box, because who wouldn’t want to be gifted such a special set?

Or, what about the classic ankle boot for toddlers in a striking bright blue color?  These will definitely turn some heads.

Timberland Timberland Boys’ 3 Eye Chukka are some of the classiest toddler shoes we’ve ever seen. Sleek leather uppers and thick textured soles combine for some serious style in these boots.

Though there are many, many, more glorious Timberland boots and shoes for kids, we will finish up with these classic navy ankle boots that toddlers, little, and big kids will all love with their jeans.

Bottom Line

Timberland simply can’t be beaten on selection in all categories. However, Caterpillar definitely can come out on top in specific styles, particularly in men’s and women’s boots and women’s styles. So there may well be times when it’s certainly worth your time to check out what Caterpillar has to offer before heading over to see if Timberland has anything you like better.

Overall, it’s hard to make an argument for spending much time scouting out Woodland products. There simply isn’t enough of a selection, or even distinctive enough differences within categories, to make it worth your while.

And, of course, if you want some tough little boots for your kiddos there is only one place worth visiting among the three and it is more than worth your time. In fact, the children’s shoes available from Timberland are so fabulous you may have a difficult time pulling yourself away…or staying within your budget.

In either case, Timberland or Caterpillar, you can be sure of ending up with a quality product that looks great.