Last Updated: April 21, 2022
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Red Wing vs. Timberland (Who Makes Better Boots?)

Both Red Wing and Timberland are kind of iconic when it comes to footwear. Red Wing is best known for its amazing range of high-quality work boots and their premium craftsmanship.

Timberland, on the other hand, is much more mainstream and fashionable and makes great everyday boots.

But, Red Wing is not far behind in that respect. Their Heritage collection is comprised mostly of everyday boots, and I will therefore focus on that range in this review.

We will take a look at the most iconic shoes from both these manufacturers, and compare all of their important characteristics. And we will do that for both men’s and women’s shoes.

So sit back and relax, and join me in this detailed comparison of the best footwear by Red Wing and Timberland!


Red Wings vs. Timberland: Men’s Shoes

In this part of the review, we will check out and compare the different types of men’s shoes that these brands have to offer.

The Classic Style

Red Wing Heritage Men's Classic Work 6" Round-Toe Boot

Red Wing Men's 8181 6' Classic Round Boot,Hawthorne Muleskinner,10.5 D(M) US

These boots are Red Wing Heritage classic, both because of their design and material. They are made of leather, and they are water-resistant. But, in order to get the most out of that functionality, you will have to get either a waterproof spray or wax.

In terms of sizing and fit, Red Wing suggests that you order these in half a size bigger than you usually wear, particularly if you plan to put an orthopedic footbed in them. Additionally, you will have to break them in, and that could last for a while.

In fact, one customer on Amazon said that it took them almost two months to break these in, which sounds like a lot of work. But once you do break them in, they will be as comfy as a pillow.

Overall they are comfortable and good-looking shoes. You can really see that the craftsmanship that went into these shoes is amazing.  But I think Timberland has the upper hand in this round, and we’ll see why below.

Product Information

  • Material: Hawthorne Muleskinner Leather
  • Insulation: No Information
  • Waterproof: Water-resistant
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Winner: Timberland Men's 6" Premium Waterproof Boot

Timberland Men's 6' Premium Waterproof Boot Fashion, Wheat Nubuck, 10

I think everyone owned a pair of these, at one point in life. They are truly the classic Timberland booties, and probably the first thing that comes to mind when someone says “Timberland” to you.

They are waterproof and insulated, and they are great winter boots. They will stay waterproof both in snow and in heavy rain, which is super important. And best of all, they really are comfortable.

However, they are not comfortable out of the box; you will need to break them in. They are a little stiff when they are new, but once you properly break them in, they will be your favorite winter boots. And it shouldn’t take too long to break them in, just a few days.

The best thing about these Timberlands is that they are incredibly lightweight, which often isn’t the case with winter boots. And they are mostly true to size; I think that you could go half a size down with these, for a really snug fit. They do become a little wider when you break them in, so keep that in mind.

Product Information

  • Material: Leather
  • Insulation: 400g of Primaloft
  • Waterproof: Yes
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The Boots

Red Wing Heritage Men's Moc 8" Boot

Red Wing Heritage Men's 8' Classic Moc Toe Boot, Oro Legacy, 8.5 M US

In terms of style and design, these are probably the best-looking boots in this review. The leather just looks luxurious and gorgeous, and they look incredibly well made. However, they lack some pretty important features to be considered a great winter boot.

For one thing, these Red Wing boots are not insulated. And what’s even worse, they are not waterproof. They are somewhat water-resistant, and you would be fine in light rain. However, if you were to step in the puddle in these, your feet would get wet instantly.

And that really is a shame. You could spray them or something to make them waterproof though, so half of the issue can be fixed. But there’s one more issue; they are really stiff out of the box. That means that you will have to break them in and that process could last a while.

So yes, they do look gorgeous and rich, but they are definitely not the best winter boots out there. However, they are pretty good fall boots, so you can get them for that season. Just remember to order them in half a size smaller than you normally wear, for the perfect fit.

Product Information

  • Material: Oro Legacy Leather
  • Insulation: None
  • Waterproof: No
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Product Information

  • Material: Full-grain leather
  • Insulation: None
  • Waterproof: Yes
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The Oxfords

Timberland Men's Icon Premium Waterproof Oxford

Timberland Men's Icon Premium Waterproof Oxford, Wheat Nubuck, 14 C US

On the one hand, I can understand that Timberland wanted to stay true to its overall aesthetic. On the other hand, these shoes don’t really look like Oxfords. I don’t know if it’s just me, but they kind of look like someone took a classic Timberland boot and just cut off the part that goes over the ankle.

But, what they lack in looks they make up for in functionality. These “Oxfords” are waterproof, which is a really convenient benefit. Because of that, these shoes are not only good for the winter, but also for spring and fall.

However, when I think of Oxfords, I think of light shirts and khakis and warm weather. And these are not really suitable for summer weather, because they are heavy and bulky. Honestly, can you imagine yourself wearing these when it is 35+ degrees Celsius? I didn’t think so.

Overall this is a good, sturdy shoe. They do need to be broken in, but that process shouldn’t last longer than a week. My only issue with these Timberlands is that they are labeled Oxfords and I had certain expectations because of that. But I’m rambling on about their design; apart from that, they are perfectly comfortable and functional shoes.

Product Information

  • Material: Premium Waterproof Leather
  • Insulation: None
  • Waterproof: Yes
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Winner: Red Wing Heritage Men's Weekender Oxford Work Shoe

Red Wing Heritage Men's Weekender Oxford, Copper Rough & Tough, 7.5 D US

The Oxford shoe is truly a classic shoe style, so it’s not surprising that almost every brand has Oxfords in their range. I was actually surprised that even Red Wing has them because their main focus are boots.

But they do have Oxfords, and they look amazing. They are made of premium leather, and they are hand-stitched. This also means that, should you need to, you can have them recrafted.

In terms of sizing, these tend to run large. Because of that, you should order them a (half) size smaller than what you usually wear. And there will be a break-in period; they are made completely out of leather, after all.

But the good news is that the break-in period is short, and after just a few days they will become much softer and much more comfortable.

One more thing; this is not a winter shoe, and so it’s not really important if it’s not insulated or waterproof. These Oxfords are perfect for the upcoming spring days. Just pair them with a pair of khakis and you will get that effortlessly cool, modern look. :>

Product Information

  • Material: Copper Rough & Tough Leather
  • Insulation: None
  • Waterproof: No
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Red Wing vs. Timberland: Women’s Shoes

In this section of the review, we will check out the women’s shoes. So ladies, sit back and enjoy! :>

The Classic Style

In this round, it was impossible to determine a winner. The Timberlands have the upper hand in terms of their weather resistance and warmth, but the Red Wings have a much sleeker design and are made of higher quality material. Therefore, both of these classic boots are winners for me.

Timberland Women's 6" Premium Boot

Timberland Women's 6' Premium Waterproof Boot, Wheat Nubuck, 9 M US

Timberland Women’s 6″ Premium Boots are very similar to their men’s counterparts. The design is the same, the functionality is the same; in fact, they only differ from the men’s version when it comes to their sizing and color variety.

So to sum up a few facts I already mentioned about the men’s shoes, these are very comfortable and lightweight. They are waterproof and will help your feet stay dry in both rain and snow. In addition to that, they are insulated and they will also keep you very, very warm.

The main difference between the women’s and the men’s shoes is in the variety of colors. And, even though there is a lot of variety for the men’s shoes, there is even more variety for the women’s. Grey, black, pink, purple, print – you name it, Timberland has it. Overall, they are high-quality, multi-functional boots and every woman should own at least one pair of these.

Product Information

  • Material: Leather
  • Insulation: 200g of Primaloft
  • Waterproof: Yes
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Red Wing Heritage Women's Iron Ranger-W Boot

Red Wing Heritage Women's Iron Ranger Work Boot, Amber Harness, 6.5 B US

In terms of design, the Red Wing’s classic boot for women looks phenomenal. It looks much more elegant than the Timberland boot, and it really looks like something you could wear with skirts and dresses.

The Iron Ranger Boot is made of premium, high-quality leather, and it is hand-stitched. You have to appreciate the craftsmanship that goes into these shoes; they truly are a piece of art.  And yes, the leather means that they are going to have to be broken in, so be prepared to spend about a week doing just that.

In terms of sizing, they are mostly true to size. They are, however, somewhat narrow, so if you have wider feet, go half a size up. But, the boots will get wider as you break them in, so don’t worry about that too much.

As for their weather resistance, they are not completely waterproof. They are water-resistant and they should keep you dry in some light rain. However, stepping in a puddle will get your socks soaking wet. Additionally, you can treat these with waterproof sprays and waxes, and that would really help enhance this feature.

Product Information

  • Material: Amber Harness Leather
  • Insulation: None
  • Waterproof: Water-resistant
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The Dress Boots

Red Wing Heritage Women's Short Engineer-W Boot

Red Wing Heritage Women's Short Engineer Work Boot, Copper Rough and Tough, 8.5 B US

In terms of style, I have to say it’s somewhat disappointing that Red Wing Heritage collection does not feature a pair of tall boots for women. These are medium tall, which means that they go just a few inches above your ankle.

The Engineer boots run true to size, so you’ll be fine if you get them in your usual size. They are a little bit narrow, but that problem goes away once they are properly broken in.

They look good and classic, and you could wear these with anything, which is always a bonus. Additionally, you can get them in several different colors, so opt for the ones that you like the best. But keep in mind that these shoes aren’t insulated or waterproof, so they aren’t really great for wet weather.

Product Information

  • Material: Charcoal Chinook Leather
  • Insulation: None
  • Waterproof: No
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Winner: Timberland Women's EK Bethel Tall Harness Boot

Timberland Women's EK Bethel Tall Harness Boot,Brown,6 W US

Now, this is a pair of tall dress boots. They look really gorgeous, and I’m sure that you could wear these boots with almost anything. Sadly, you can’t wear them in any type of weather. For one thing, the upper part of the Bethel boots is suede, which is rarely waterproof. In fact, in most cases, suede shouldn’t even be exposed to water because it could stain it permanently.

Therefore, treat these babies with a waterproof spray as soon as you take them out of the box. That will not only prolong their life but also help keep your feet as dry as possible. The lower part of the boot is made of leather, which is pretty water-resistant on its own.

They run true to size, so your normal shoe size should fit you perfectly. And, since these are so tall, you are also probably wondering about the calf-fit. These boots actually have an elastic insert at the very top, which means that they should fit women of all sizes. In fact, they also tend to be quite wide, so if you have very skinny calves, they might be too wide for you.

Overall, they are comfortable and good-looking dress boots. But in terms of their functionality during freezing winters, you will be better off with a classic Timberland boot than with these.  But beautiful doesn’t always translate to functional, right?

Product Information

  • Material: Leather
  • Insulation: None
  • Waterproof: Water-resistant
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The Heels

Red Wing Women’s Clara Boot

Red Wing Heritage Clara Oro Legacy 9.5 M (B)

Red Wing’s focus on work shoes becomes more and more obvious when we try to find some dressier footwear. These boots are basically the only “high-heeled” women’s boots in their range. And honestly, that’s a little bit sad.

In terms of craftsmanship, the Clara boot is a premium piece of footwear. It is hand-stitched and made of high-quality oil-tan leather. There is not a doubt in my mind that these boots would last you for years, if not decades. But, would you want them to?

In terms of their design, they look a little bit awkward. The leather is gorgeous, however, the height of the heel is what makes them look weird, at least to me. So, if I were looking for a premium-quality high-heeled boot, I would have to go with the Timberland ones.

But, that is purely from a design standpoint and says nothing about the quality and comfort of these boots.  They are very comfortable, and more so once they are properly broken in. And in terms of sizing, you should get them in your regular size – they should fit nicely.

Product Information

  • Material: Amber Harness Leather
  • Insulation: None
  • Waterproof: Water-resistant
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Winner: Timberland Women's EK Glancy 6 Inch Boot

Timberland Women's Glancy 6 Ankle Bootie, Dark Blue, 7.5 M US

It is not often that you can find functional, high-heeled boots. That is why I am extremely glad that I stumbled upon these shoes on Amazon!

For one thing, these boots have a rubber heel, which means that they are perfectly suitable for wet and icy pavements. The rubber sole and heel have plenty of traction, but there’s another benefit to them. Wooden heels deteriorate much faster than rubber ones when they are constantly exposed to water/snow.

In terms of sizing, I would recommend that you buy these in half a size larger than what you usually wear. This is because they are quite narrow in the toe area, and you could benefit from the extra room there.

Unfortunately, they are not waterproof. They are water-resistant, and you can reinforce their resistance by treating them with a waterproofing product. Other than that they are really good boots that are not only stylish but also really warm and comfortable.

Product Information

  • Material: Full-grain Leather
  • Insulation: No Information
  • Waterproof: No
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What To Look For

Style

To make the review as fair as possible, I decided to divide both the men’s and women’s sections into three categories: the classic shoe, the boot, and the oxford/heel for men/women, respectively.

So, if you already have a specific style of shoe in mind, feel free to jump to it via the quick navigation above. Otherwise, check out all of them, and then decide which style you feel you would be the most comfortable with.

Note: Timberland focuses the most on creating shoes for everyday wear, and that will be the main focus of this review. However, Red Wing’s primary focus is working boots, and you can read more bout those in another review I did recently. I decided to focus more on the everyday shoes in this review because comparing a work boot to a casual boot would be like comparing apples and oranges. :>

Comfort

Comfort should always be at the top of your priority list when you are choosing new boots. No matter how good they look, they have to be comfortable; otherwise, you are just stuck with a pair of unwearable boots. How do they fit, how much do you need to break them in, will your feet start to hurt after 6 hours in them, etc.; these are all questions that you need to seek answers for.

I will talk about the comfort of each shoe, and try to pull from the experiences of real people who have worn and owned these shoes for years. I will also try to give you information about the break-in time of the shoes since I find that to be a really important factor.

Materials

When choosing the right boot it is very important to know what kind of material it is made of. Some materials will require a longer break-in time than others, some are waterproof while others aren’t. The latter is particularly important because we will be talking about boots for the most part, and boots should always be waterproof.

I will list that information in the product information box for every product, and be on the lookout for that. I will also tell you precisely what each shoe is made of so that you can then know how to properly care for it. Taking care of a pair of boots has a huge impact on their lifespan, which is why it is so important.

Red Wing vs. Timberland: Which Shoes Should You Buy?

Now that is a tough decision. I would have to say that Timberland shoes are kind of better overall. There is more variety, they are less expensive, and a much bigger amount of the shoes is waterproof and insulated.

Therefore, they are obviously the better option for winter boots, particularly if you live in an area where it snows a lot. In that case, I would definitely recommend the Timberland Classic boot, to both men and women.

Timberland Men's 6" Premium Waterproof Boot Fashion, Wheat Nubuck, 10
  • TIMELESS ICON, the Original Yellow Boot has been breaking cultural and societal barriers for over 50 years
  • ALL-SEASON-STYLE gives you tireless waterproof performance and instantly recognizable work-boot style
Timberland Women's 6" Premium Waterproof Boot, Wheat Nubuck, 9 M US
  • Classic boot in waterproof leather featuring lace-up front with rustproof hexagonal eyelets and heavily-padded collar
  • Logo embossed at side heel

On the other hand, Red Wings are truly iconic. Almost all of them are hand-stitched, and the craftsmanship that goes in these shoes is something you can rarely see anywhere else. Because of that, they are also incredibly durable; in fact, I know people who have owned the same pair of Red Wings for over a decade.

Yes, the wear and tear are obvious, but they still haven’t fallen apart completely. I would definitely suggest the Red Wing version of the Oxford shoe for men because they are not only incredibly good-looking but also very comfortable.

Red Wing Heritage Men's Weekender Oxford, Copper Rough & Tough, 7.5 D US
  • Blind eyelets
  • Atlas tred sole,buy Red Wing Heritage footwear 1/2 size smaller than their normal size

For women, I would have to say that the classic Red Wing Iron Ranger boot is also a great choice. They are elegant, stylish, and very comfortable.

But, for women who want to get something practical in a high heel, I would have to go back to Timberland. They have much more variety and the EK Glancy boot is a great high-heeled choice.

Timberland Women's Glancy 6 Ankle Bootie, Dark Blue, 7.5 M US
  • Upper made with premium leather from an lwg silver-rated tannery
  • Padded collar

Overall, both of these manufacturers make premium quality shoes. And the bottom line is to get the boots that you like the most; everyone has different taste, and what might work for me, might not work for you. That’s why you should head over to Amazon and get check out all of them!