Timberland Chukka Boots

9.2 score
[Editors rating (9.2)] = (WalkJogRun) score (9.2)/10

Editor rating: 9.2 / 10
User's rating: based on 0 user ratings
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Editor’s Conclusion
Whenever Timberlands land in front of me to review, I always get excited. I love the brand, I love the designs, I love the craftsmanship. Timberland has been around for decades and not just because they are popular, popularity will only take you half the way.

They are renowned for making boots that well outlast the price you pay for them. You know that the moment you put a pair of Timberland boots on, your style level has gone from a 5 to a strong 9!

The Timberland boots we’re about to look at are stylish, durable, classic, and comfortable. Yes, if you’re looking for a pair of boots that you can pair with pretty much any outfit and will have heads turning or people commenting on your shoes, then you’re search is over.

My friends, let me introduce to you the Timberland Chukka boots. A classic and well-built boot that will have you at the envy of all your friends and will provide you with the utmost comfort.

They ooze style, give the cushioning your feet deserve and will make a great finish to almost any outfit.
Timberland Chukka Boots Review Facts
Editor's Pros & Cons



Three-layer SensorFlex technology


Sizing can vary – be sure to check you buy the right size

Key Features


The Timberland Chukka boots are designed with the highest of quality materials, Nubuck leather for that flexible and stylish finish, and a nice comfortable boot. Three-layer SensorFlex technology gives you even more flexibility and an Ortholite footbed keeps feet fresh, cushioned and supported.

These casual boots have a padded collar to provide cushioning and support to the ankle. Cotton laces are both great for strength, as well as style. The tongue has the Timberland logo on a textile material for that added fashion statement and an imprint of the logo on the heel.

You also have the option of different colors so if the tanned yellow isn’t something you would choose, then you have at least 4 others that you can take a peek at. I know, bonus!


Timberland is a brand that is nothing if not durable, they make strong and sturdy boots that will last you years. The Nubuck leather is used for its strength and resistance to wear. It also feels like a suede textile rather than normal leather.

The EVA midsole is a welcomed cushion for your feet and means you will be able to last longer in these shoes too. Rubber outsoles are the best fit for durability and are a great material on wet and dry surfaces.

All being said, these boots are going to last you well and provide you with the utmost comfort and cushioning.


The Timberland Chukka boots are far from uncomfortable, they have an Ortholite footbed that will give you great comfort and will keep your feet fresh.

Nubuck leather is great for flexibility (your feet will have time the chance to move about) and the collar is not only a fashionable add-on but great support and cushion for the ankle as well.


With fashion comes a price, it’s inevitable, you cannot get quality without paying for it. I would honestly say though that I find the Timberland Chukka boots to be reasonably priced given the brand and their style. They are such a versatile boot that you will get your money's worth out of them.

I pride myself in buying quality products, and I would always buy my partner the best too, so the price of the Timberland Chukka boots is not something that I find would waver me picking these boots.

Comparison to Similar Boots

If you’re just not into the Timberland Chukka boots because they aren’t your style or are too pricey, you should check the Rockport Rugged Bucks II or the Ferro Aldo Birt Chukka boots.

Both options are a lot less in price compared to the Timberlands, but they are similar in style and design. Made from durable leather, a memory foam insert for comfort, and a rubber sole for durability. They are a good contender if you are wanting to have a casual boot for less of a price.


The Timberland Chukka boots are a great model. They are stylish, versatile, reasonably priced and use quality materials that will last you.

Considering your options is important before purchasing any pair of boots. Don't just wing it, check the details, and make sure they will be the right fit for you. I'm a big fan of Timberland as it's a brilliant brand as far as quality craftsmanship goes and you're not going to be disappointed pairing these boots with any outfit.

In my opinion, if you're wanting a casual shoe that will last you a long, long time, then these boots are worth a look.