20 Best Timberland Hiking Boots for Adventurous Hikers

Best Timberland hiking boots

Ever looked at mountain hikers with wishful eyes?

Or, ever wondered what it would feel like to go through those steep and slippery terrains, living off the land?

Think it’s a good feeling?

Well, you’re right. Hiking can be real fun… with the right footwear. Whether it’s the mountain or the countryside, when hiking, you want shoes that won’t demand too much effort of you to move.

At the same time, you want something that’s sure-footed and won’t easily give in to all the slippery surfaces. Am I getting these right?

Even more than all these, you want to be comfortable. You need a comfortable shoe to enjoy hiking, not one that’ll cause you sore feet at the end of the day.

Bearing all these in mind, we have put this list together, of the best 20 hiking shoes by Timberland, one of the best boot makers in the market. Read carefully and take a pick.

6-Inch Waterproof Field Boots

Best Timberland hiking boots

Going on hiking, it is very likely that you’re going to come across a whole bunch of puddles. This is especially true in the countryside.

That is why this particular boot has been made waterproof for your use. It is made of waterproof leather uppers that will surely keep your feet dry in all conditions.

Another important fact to consider is the comfort of the shoe, so your feet don’t get sore along the way (at least not more than they have to be). For this, the field boots come with a padded collar and an anti-fatigue technology footbed.

The outsoles, finally, are made of polyurethane; a waterproof, slip-resistant material that will make you not worry about skid.

This shoe has a lace-up closure and can be worn with jeans or even chinos. A pair of them cost about $180.


  • Waterproof timberland boot
  • Comfortable
  • Incorporates an anti-fatigue technology
  • Lightweight
  • True to size


  • Snake fangs might penetrate through the mesh part

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Mt. Maddsen Mid Leather Waterproof Hiking Boots

Comfy Timberland boots for hikers

With this Timberland Mt. Madden mid-sized boots, you can hike on whatever terrain that catches your fancy as it provides protection and comfort to your feet. The shoe’s uppers are made of waterproof leather to protect your feet from rain other water bodies.

It also has an internal TPU shank, which works with the compression-moulded EVA midsole to provide torsional rigidity and serve as the major shock absorber.

On the insides, anti-fatigue insoles are present to provide comfort while you glide easily through the terrain. The 15% recycled rubber outsoles provide great traction and skid-resistance, while the gusseted tongue keeps out debris. This shoe has a lace-up closure and costs about $90.


  • Comfortable
  • Has anti-fatigue technology
  • Highly skid-resistant
  • Waterproof hiking boot


  • It is not for wide-footed hiker

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Keele Ridge Waterproof Hiking Shoes

Comfortable hiking shoe by Timberland

For hikes that are not particularly long, you might want to go for the Keel Ridge hikers. It’s got waterproof uppers; durable full-grain leather uppers.

On the inside, the leather is mesh-lined for breathability. This helps deal with feet odour, moisture and general irritation.

On the insides, the Ortholite insoles are present to provide well-cushioned comfort. The outsoles are made of 34% recycled rubber, stretching out to the toe-tip area of the shoe to serve as protection.

This rubber is great for traction and is known to be durable. The shoe is lace-up and goes well with a pair of jeans. It also has a pull tab for easy wear and removal. A pair of them cost about $100


  • Properly cushioned
  • Great rubber sole traction
  • Made with waterproof leather upper
  • Breathable
  • It is true to size


  • The tongue which extended from the lacing isn’t waterproof

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White Ledge Mid Waterproof Hiking Boot

Best Timberland trail boots

The White Ledge Mid-sized boot is made for hiking in style. The best things about the shoe begin not with its good looks but with its premium nubuck leather uppers.

It has a seam-sealed waterproof construction that protects the boot itself and keeps the water from slipping through holes to your feet. The uppers are lined internally with ReBOTL recycled fabric to improve breathability.

The sole assembly is made of well-cushioned EVA midsoles and insoles, and rubber outsoles with multidirectional lugs that offer great traction in several terrain orientations.

Its well-padded collar and the rustproof, speed lace lacing system offer secure closure. A pair of these go for $113


  • Good cushioning system
  • It’s waterproof
  • High traction rubber sole


  • You might have problems with the size.
  • It might also be too stiff (depending on your choice anyway)
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Euro Hiker Boots

Best hiking boots by Timberland

This is a world-class hiking boot that is popular, not only for performance but for its looks as well. Its uppers are made of a combination premium full-grain leather and CORDURA® nylon materials. The CORDURA material comes in handy when hiking through terrain with lots of debris.

The sole assembly here consists of an EVA midsole (for cushioning and shock absorption), a steel shank (for arch support and a bit of shock absorption as well), and a 34% recycled rubber material.

The combination of these qualities provide top-notch traction and considerable comfort. You could own one of these for $115.


  • It is waterproof
  • High traction outsole
  • It is true to size
  • Comfortable


  • Sole may collapse due to daily rugged usage
  • Sometimes, the glued sole pulls

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Flume Mid Waterproof Hiking Boots

Timberland best hiking boots

Named after the famous Flume Gorge, this shoe was designed to hike even steep paths as that at the foot of Mount Liberty. It is designed to keep your feet both comfortable and protected through the hours of walk.

It is made of the traditional full-grain leather uppers with waterproof construction to keep the feet dry. The footwear also has the multidirectional lugs on the rubber outsole that improves traction in every way and on every terrain.

Finally, the EVA midsole pads the shoe’s collar, serves as footbed and absorbs shock with each stride. It costs $115 to get one.


  • It is waterproof and keeps your feet dry
  • Its EVA midsole serves as a comfortable footbed and shock absorber
  • The comfort is top-notch
  • It is supportive as it offers ankle support.


  • A bit pricey for the quality
  • Not the best option for wide-footed hikers.

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Chocorua Trail 2.0 Waterproof Hiking Chukka Boot

Top-rated Timberland boots for hiking

Another Timberland that’s known for the bit of ruggedness that it adds to one’s outfit is the Chocorua. With the high ankle, high tongue design, it adds that little fire to your looks.

It’s got the waterproof leather upper combined with mesh material for breathability. It is lined on the inside with Gore-Tex material.

For the sole assembly, there’s the EVA midsole which pads the collar, cushions the shoe all-round from within and works as a comfortable footbed. The outsole is made of strong, durable, and most importantly, skid-resistant rubber.

Enjoy every step of you your hike with these beauties. A pair would cost you around $110.


  • Provides ankle support
  • It is not only water-resistant, but waterproof due to the Gore-Tex leather upper.
  • It is comfortable to wear
  • The removable insole helps you to easily maintain the pair or insert your favorite insole


  • The toe-box runs narrow
  • It is not true to size

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Field Boot Mid Hiking Shoe

Best Timberland trail shoes

You could be a tourist, planning a tour of a mountainside or other steep terrains. So, you wouldn’t want to wear something that’ll make you look odd among others, or that would make your steps unsure.

The Timberland field hiking boot is for you. It has a near regular shoe look, but all the performance benefits of a hiking shoe.

From the nubuck leather uppers to the padded collars, the boot provides utmost comfort for all-day wear. The direct-inject polyurethane midsole is lightweight and provides cushioned comfort as well. They also serve as shock absorption techniques.

It’ll cost you around $150 to get these.


  • Comfortable
  • High traction for any kind of terrain
  • It doesn’t run narrow hence it is good for wide footed hikers


  • It is not waterproof

Note! There are two versions of this boot. One comes with the usual Timberland metal emblem. This one, however, doesn’t.

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1978 Aerocore Hiker Waterproof Ankle Boot

Best comfortable boots for hikers

Here is another sample of a multipurpose hiking shoe. It has got the looks of your everyday sneaker, with the performance of a hiking boot.

The uppers are made of premium waterproof leather, seam-sealed to prevent water from finding its way through. The collars are well padded for comfort, as is the entire shoe via a well-cushioned midsole.

Finally, the sole is made of synthetic rubber, flexible, durable and with carve patterns for traction on various terrains. Besides that, this boot also looks good as an everyday walkabout shoe.


  • It’s waterproof
  • Lightweight with great support from the insole
  • Removable insole
  • Great ankle support
  • Suitable for cold weather because of the proper insulation
  • It is true to size; so order your normal size.


  • A bit stiff
  • Offers good grip but not for rugged terrains

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Oakwell 7 Eye Lace-up Boot

Comfy Timberland boots for hikers

It is almost impossible to wear boots like these and walk into a room without feeling at least a little badass. This is a high-ankled shoe with nubuck leather uppers and a whole lot of cushioning for your comfort, especially at the collar area.

The shoe also has well-cushioned midsoles and a strong lace-up set-up for closure. However, it is made of strong, durable rubber.

It is patterned into multidirectional lugs at the bottom for traction across different surfaces. This is a great hiking, as well as all-day shoe. A pair costs $100


  • It is stylish yet tough
  • The footwear is well cushioned and so it is comfortable
  • It is lightweight
  • Has well toothed outsole for the hiking spree.
  • It is appropriate for every season of the year


  • Not waterproof
  • Inappropriate for cold weather because it is not insulated
  • It is a bit narrow

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Radford 6-Inch Outdoor Ankle Boots

Outdoor Timberland boots for hiking

This Timberland boot stands tall as one of its top boot designs. It features the SensoreFlex tech outsoles, which is one of their top traction technologies.

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The shoe itself has full-grain leather uppers, with seam-sealed construction to keep them waterproof. The collars are heavily padded to provide you with maximum comfort.

The sole assembly contains the previously mentioned SensorFlex outsoles that support as well as absorb shock to the feet.

Right above them are the EVA footbeds that also give you that lightweight, comfortable feeling with each step. They go for $198


  • Waterproof hiking boot
  • It is comfortable and lightweight
  • Keeps your feet warm due to its insulation features
  • Great ankle support
  • High traction rubber outsole for all terrains


  • It’s pricey

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Courmayeur Valley 6-Inch Waterproof Boots

Best women's hiking boots

This is s dream hiking boot for women. These boots are perfect for walking in various weathers. Unlike other boots, they have wool/cotton herringbone lining which provides warmth and makes it perfect for even hiking even in the snow.

The uppers are made of Leather; waterproof leather while the insoles are made of wool/cotton two-part flex.

Moreover, the outsoles of the shoe are rubber-made, with multidirectional traction lugs. Directly above the outsole is the EVA foam midsole for rebound cushioning; absorbing shock and providing comfort.

The shoe is available at $180.


  • A waterproof hiking boot for women
  • Good insulation proper for cool weather
  • Lightweight and stylish


  • It is narrow and wouldn’t fit hikers with wide feet.

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Chillberg Insulated Winter Boots

Lace-up hiking boots by Timberland

Got any plans to take a little hike during harsh colds? Or do you just have to visit specific places through the snows?

The Timberland Chillberg has got you covered, or your feet at least. Besides the premium waterproof leather that ensures your feet don’t get wet and the boots don’t get soaked, there’s also about 400g of PrimaLoft® insulation from the collar to the toe tip area to keep out the worst of the weather.

The lining beneath the uppers is made of 100% PET fleece to support the PrimaLoft material in keeping out the cold. There’s also the sole assembly consisting of the EVA midsole that supports, absorbs shock and provides further cushioning and makes a comfortable footbed.

The lug outsole is made from 34% recycled rubber and serves as an anti-skid mechanism. The final piece in this fortress footwear is the gusseted tongue that keeps out debris. A pair of these cost $150.


  • Good insulation for snow and cool weather
  • Stylish and comfortable
  • Great price for the quality
  • It is waterproof and lightweight
  • Well-toothed outsole for great traction.


  • The boot runs big
  • Users have reviewed that the previous version of the boot is better.

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Plymouth Trail Waterproof Hiking Boots

Timberland Hiking boots

These are another pair of boots that serve you whether you’re hiking or just chilling. They have the premium waterproof leather uppers, laced with abrasion-resistant fabric so the boot looks new for as long as possible.

The uppers are lined with GORE-TEX® material that enables breathability and further prevents water from penetrating.

The sole assembly consists of an EVA midsole/footbed for cushioned comfort and a skid-resistant rubber outsole. The collar is well-padded for comfort and the hard rubber sole extends to the toe-tip to protect toes from impact. This shoe costs $140.


  • Lightweight boot with waterproof features
  • Stylish and comfortable
  • Great support on the ankle and footbed


  • The run narrow
  • The waterproof feature is not too strong

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Brooklyn Waterproof Low Hikers

Waterproof hiking boots for hikers

Seldom will you encounter a pair of boots that tries to keep itself clean even while your run/walk. However, the Defender Repellant Systems® treatment helps this pair achieve just that.

The uppers are made of Better Leather, with this defender system repelling everyday stains on the go. That way, it becomes easier to clean and maintain the shoe. These uppers are lined with ReBOTL material for breathability.

Also, the sole assembly consists of lightweight Ortholite insoles, Aerocore energy system midsoles that are known for their high rebound cushioning.

Finally, the outsoles are made of rubber lugs, made in multiple directions for various terrains. These self-preserving hikers are available at $140.


  • Offers good support on the ankle and footbed.
  • It’s waterproof and lightweight
  • Comfortable hiking boot
  • Well-toothed outsole for rugged surfaces


  • It runs big

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Garrison Trail Hiking Sneakers

Best Timberland trail shoes for hikers

As the name suggests, these are hiking sneakers. This means you could wear them to hit the gym, to work, for sports, for early morning runs, or even with your casual outfits to class or work; anywhere. They are as beautiful as they are effective.

These light sneakers are made with synthetic leather uppers and lined with ReBOTL™ fabrics for breathability. The forefoot area is a laced with water-resistant material in case you run into puddles.

The midsole is made of EVA material, for top-notch cushioning and outsoles are made of rubber. This rubber is lugged using TimberGrip™ traction technology and is anti-slip and durable. $120 and you have these in the bag.


  • It offers a remarkable traction on all terrains
  • Stylish and comfortable boot
  • Proper cushioning and great support on the footbed
  • It’s affordable


  • It is not wholly waterproof but it’s breathable

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Mt. Major Mid Hiking Boots

Timberland hiking boots for men

The Mt. Major hiking boots are made with the terrain of the Mt. Major, New Hampshire in mind. Its outsoles are made with solid rubber, having multidirectional lugs to easily glide through such steep environments.

To support it, there’s a compression-moulded high-rebound EVA midsole to support your strides and provide comfort as you move.

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The uppers are made of Better Leather and have a fully-gusseted tongue as well to keep out the debris. More so, the lace hooks are of speed lace, rustproof hardware, so you don’t have to worry about them getting old quick. You can get a pair for about $85.


  • Comfortable hiking shoe
  • It is lightweight and durable
  • Good price for its quality
  • Available in many sizes — wide and narrow
  • It is stylish and warm


  • The waterproof feature is questionable
  • The material is not the best quality of material

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Redwood Falls Waterproof Mid Hiking Boots

Waterproof Timberland hiking boots

These Timberland Redwood Falls boots are made for performance. It is made of Better Leather uppers and a TimberDry™ waterproof membrane. It also uses rustproof lace hooks and a ReBOTL inner lining for breathability.

The shoe has got a well-padded collar, and an EVA midsole for cushioning and high-rebound support. It also has lightweight Ortholite insoles and a Gripstick rubber outsole with multidirectional lug designs for top-level traction.

For $150, you could own this lovely pair.


  • Highly waterproof
  • Comfortable and lightweight boot
  • Great price for the quality
  • Good support on the ankle and footbed
  • Strong grip rubber outsole


  • None is visible yet

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Euro Hiker Knit Mid Hiking Boots

Best Timberland hiking boots

Want to hike in style? Or do you just want a sweet looking shoe that makes you feel a bit razz?

This is one you should consider. The shoe has coated CORDURA® nylon uppers and rustproof lace hooks. The uppers are lined with ReBOTL material to aid breathability and an EVA midsole for support and comfort.

The soles are made of rubber, lugged for optimum traction and between the collar padding, there’s a steel shank for arch support.

All these make the shoe as easy to move in as they are comfortable. At $100, they’re a valuable addition to your wardrobe.


  • Stylish and comfortable boot
  • Great for cool weather
  • Maintains high traction
  • It is lightweight and made with good materials


  • Not a waterproof hiking boot

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Field Trekker Mid Boots

Top-rated Timberland hiking shoes

These boots are made to suit both athletic and adventurer needs. It’s got a mid-level height and the sleek look of a sneaker but with the right performance qualities of a hiker.

Beginning with the uppers, they are made up of premium leather, lined with breathable materials.

The sole assembly consists of the Ortholite insoles; the comfortable footbed, the compression-folded EVA midsoles; for support and cushioning, including in the collar padding, and the rubber lug outsoles.

These are made skid-resistant and are as durable as the shoe itself. Rubber rand protects the toe tip from impact. This pair is available for $130.


  • Comfortable outdoor boot
  • Has good ankle support
  • Made with good quality materials
  • Provides good traction
  • It is stylish yet lightweight


  • It not a good choice if you’re looking for a waterproof boot

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Do you really need hiking boots?

Yes you do. Hiking boots gives you that support, stiffness, and grip you need to traverse all terrain and surfaces.

If you decide to go for other kinds of shoes not designed for hiking, you might end up not enjoying the escapade, or even sustain an injury.

Here are quick reasons why you should wear hiking boots on a hike:

  • They provide you the ankle and footbed support
  • Their outsoles are designed to give you good grip
  • You need a good hiking boot to successfully pass through the muds and streams you might encounter along the hike.
  • These shoes are made comfortable fo the purpose.

Do Timberland boots last long?

How long a boot will last depends on the materials the shoe is made with and the usage. However, original Timberland boots are known for their high quality materials and construction.

So they would last for years if you take proper care of them.

Which is better between a hiking shoe and hiking boot?

Both trail runners and hiking boots are good. However, your choice for either should depend on the nature or terrain of the hike.

Hiking boots provides better support and ruggedness than hiking shoes. So if you’re hiking along a rocky or bushy and challenging terrain, a boot will be great.

Trail runners or hiking shoes are more flexible, soft and easier to walk in. So, it might be your choice for a less challenging hike.

Meanwhile, both shoe and boot provide ankle support but generally, boots are best for rough terrains.

Can you wear running shoes for hiking?

No, it is improper to wear shoes designed for running to hikes. This is because the features and requirements of running shoes are different from those of hiking shoes.

Weird Runner discussed these points in-depth; you might want to read it.


Timberland produces some of the best boots fo hiking available in the market today. As reviewed by our list, you can see the advantages and disadvantages of some of them.

Therefore, among a ton of them, we recommend these; we hope you find them worthy.

Go and leave a trail on the sand of deserts, on the rocks of the hills, and the paths of the forest.

Does that even make sense? I don’t know (smiles).

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