Red Wing VS Timberland – My Personal Experience and Review

It is no doubt that Redwing and Timberland are among the best boots that you could ever go for. However, in my experience with these 2 brands, I would highly recommend Redwing to anyone who wants real value for their money.

Note that I don’t discredit Timberland in any way whatsoever. Some of their boots are stylish, comfortable, easy to break in, and darn good looking.

However, it seems they have thrown the need for quality and comfort to the wind in the recent past while taking their prices up for no good reason.

I was a diehard fan of Timberlands in the 80’s and 90’s. The boots were really comfortable, well insulated, and waterproof. Their soles also gripped well in snow, so they were a really good option for winter.

The least I could expect from each pair was around 6 years with several resoling needs in between.

Things changed when I bought a new pair around 2010. Expecting to get a lifetime from them, the best I got was around 9 months. Tried several other models from the same brand and I had to throw them out since I couldn’t stand to be in them for over 3 hours a day.

I learn they have since been outsourced them to manufacturers in China. Most of the once comfortable and long lasting shoes are now cheaply made, unwearable, and never true to size. Sure, you could still get some American-made Timbs.

However, if you can’t tell genuine leather from the word go, look elsewhere.

Someone recommended the Redwings, and I’ve not looked back since then. The Redwings do hurt the wallet more than Timberland, but the amount can’t match the craftsmanship you get with these boots.

Why the Redwings?

There are several things that I love about these boots. First, my previous Timberland boot had glossier cheap-looking leather that couldn’t compare to the duller, fuller grain of my Redwing Moc.

Again, the Redwings don’t seem to develop creases on the toe box easily compared to Timberland which is an indication of good quality.

With the Redwings, you also get a full leather insole, steel shank, puritan stitched quarters, and a nicely welted boot which isn’t the case with Timberland.

But don’t just take my word for it. Let’s compare 2 models from these brands that are thought to compete favorably:

Redwing Heritage Moc Toe 6’’ Boot Review

In my opinion, the Moc Toe is among the best classic boots that Redwing has on its Heritage series today. This is my second pair of Heritage boots. I’ve been using the Iron Ranger for the last 5 years, and it’s still doing great though I’ve had to resole it 2 times now.

Note that I’m not entirely replacing it. It’ll probably give me 3-4 more years. But I had to get another pair to wear in between.

So, what’s there to like about Redwing Heritage Moc Toe 6’’ Boots


Build design and Durability

The fact that this boot comes from Redwing’s Heritage line speaks volumes about its durability. This boot is handcrafted in the USA. It has a tank-like design that does not seem to compromise on the style factor in any way whatsoever.

These boots feel comfortable and are also amazingly breathable. You’ll tell that they are made of super tough leather just by looking at them. However, do note that this leather may take several days to break in.

There are reports of some users who develop blisters while getting used to their boots. I didn’t experience this. It’s, however, advisable not to be in them for long hours for the first few weeks. With time, these boots mold easily to the shape of your feet thereby becoming very comfortable.

What are its dimensions?

Heritage Moc Toe has a heel measuring approximately 1-inch in height. The shaft is approximately 5.5’’ from the arch, and the platform is around 0.75 inches. The boot opening is around 6’’ all around. My pick ran a size down. So I’d highly recommend you to go for half a size down.

Are they ideal for job sites?

Sure! Besides being stylish, Redwing Moc Toe 6’’ is a real deal in terms of protection and safety. It features a copper rough and tough leather that has been triple stitched to eliminate all chances of ripping off.

Interestingly, the leather is waterproof. This makes it a reliable boot for working in damp conditions.The toughened toe box and the traction tread rubber outsole render it nicely even for construction activities.

These boots feature Norwegian-like welt construction that grows its durability multifold. It also allows you to replace the sole which is a nice feature if you want to get the best value for your money.

Tips to get the best out of Redwing Moc Toe 6’’

As I have stated before, you’ll need to go half a size down since these boots run a tad larger. Again, be patient enough to let the tough leather break in. During this time, avoid treating them before you’ve completely broken them in.

Major Drawbacks

  • Prolonged break in time – Breaking in these boots may take a little bit longer than other boots from other brands given the tough leather used. This may be an issue especially if you want to be in them for more than 3 hours right from the box.
  • Will you be walking for long? – These boots weigh over 4 pounds. This might be way too heavy to walk for long distances in. And on this note, the leather insole that comes with this boot is a joke. So you’ll have to purchase better quality.
  • They are expensive – As expected of a high-end boot from Redwing, the Moc Toe 6’’ has a higher price tag.  On the upside, this one may eliminate the hassle of shopping for and breaking in up to 10 low-end boots.

Timberland Pro Pitboss Boots Review

Timberland Pro Pitboss is another quite reliable boot that you could consider for outdoor use. One thing that I liked with this boot was its lightweight design and the ease of breaking in. This boot weighs 1lb 14oz which is  easy to move around with.

Material and durability

Timberland Pitboss is designed as a work boot. It’s crafted from Nubuck leather which promises good durability. Other materials used here include Polyurethane midsole, Cambrelle fabric lining, Nylon shock diffusion plate, and heat resistant rubber.

This boot also has Goodyear welt construction which- according to Timberland- should offer it more durability.


Is safety a concern to you? These boots have some degree of it. The sole, for instance, is heat, abrasion, and slip resistant. What I liked about the sole was that it was nicely threaded to prevent much mud from sticking.

The sole also had some support which supported my arch from excessive pressure especially when climbing ladders.  Its toe box is steel-enhanced and should offer your feet enough protection especially if you work in construction and logging sites.


Another thing that I did like with this Timberland was its level of comfort. The toe box was notably roomy– a bonus feature if you’ll be standing or walking for long hours.

I can’t also deny the fact that its innersole was much comfortable than what Redwing came with.


It’s not waterproof

This feature alone might be the reason why this boot won’t last long especially if you’ll be using in it in wet conditions. Its closed design makes it even worse. Worth mentioning, these boots are designed to protect you from electrical hazards from live circuits and apparatus.

However, the fact that they aren’t waterproof means that they won’t protect you much from electrical hazards in wet areas.

Do you like snug toe box?

We have different preferences. The roomier design might be a great relief to some and a source of discomfort to others. In fact, several reviewers wish that it was a little snug.

So, how do the Redwing Heritage Moc Toe 6’’ and Timberland Pro Pitboss boots compare?


There are a few reasons why I would highly recommend Redwing. First, it’s waterproof. This is a great feature not only for people who work in wet areas but for everyone else who’ll be using the boots for outdoor activities.

Again, with the Timberland, I did note that the steel plate at the front started popping out after several months of use. This was followed by creases on the toe box despite keeping the boots clean and treating them regularly.

Another weakness that I found with the Timberland Pro Pitboss was that the metal ties started popping off after several months. All these misfortunes haven’t happened on me with the Redwing boots.


Redwing might be a little pricier than Timberland. However, the extra bucks are really worth the premium features that Redwing offers. Timbs- especially those that are made in the US- aren’t bad in any way, but the quality can match that of Redwing. On this note, here is our other article on Redwing Moc Toe boots.




  1. Men's Classic Moc 6-Inch Boot in Brown Leather 1907,
  2. Red Wing Moc Toe Review,