James Blake
(Rated from 36 reviews)

Updated 20 January 2020 by James

I think you’ll agree with me when I say:

It’s REALLY hard to choose the best men’s timberland work boots with all the choices available!

Or is it?

Well, it turns out, that after years and hundreds of hours of testing & reviewing, we have strong opinions about what makes the best timberland work boot: anti-fatigue technology, safety and stability features, breathability.

The Timberland PRO Boondock 6” (On special until end January 2020) has all the listed elements and benefits, thus giving it an edge over its competitors. Hakeem, a student at MKU, has been using for one year now and as compared to his previous work boot choices, these have proven to be what he needs for his semi-casual and semi-official lifestyle.

Therefore, if you want work boots that have the Rigid External Heel Cup for lateral stability, the Ever-Guard™ leather heel for increased durability, and the Three-Quarter Goodyear welt/cement heel construction, the dual-density polyurethane (PU) and the thermal plastic urethane (TPU) outsole and padded top collar for comfort, then make sure you avoid the sub-standard knock-offs and get the Timberland PRO Boondock 6” from the leading supplier at the lowest price we’ve been able to find as of January 2020.

If you’re in a hurry and don’t have time for the details, here are our recommended best men’s timberland work boots.

We endeavor to only include top quality, great products that can assist you to discover what you require for your lifestyle. Our analysis is neutral and detailed because we want you to have all the facts – both good & bad before making a choice.

Top Timberland Boots for Men Overall

tims boots

Well-rounded, great value

Comfortable
Stylish and warm

Our top pick

timberland boots on sale

Awesome value

Excellent traction
Tough leather skin

* On special until end January 2020

Timberland Boots Men Review Table

Product

BEST CHOICE

Timberland PRO Men’s Boondock 6”

Timberland PRO Men’s Boondock 6″ Waterproof Non-Insulated Work Boot

  • Breathable
  • Affordable
  • Excellent traction
CHECK BEST PRICE
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MOST COMFORTABLE

Timberland PRO Men’s Gravel Pit 10”

Timberland PRO Men’s Gravel Pit 10″ Steel Toe Waterproof Boot

  • Easy on/off
  • Lightweight and a perfect fit
  • Comfortable
CHECK BEST PRICE
Read Full Review

BEST TRACTION

Timberland PRO Men’s 52565 Endurance 6” PR

Timberland PRO Men’s 52562 Endurance 6″ PR Work Boot

  • Fashionable
  • Perfect fit
  • Incredible traction
CHECK BEST PRICE
Read Full Review

MOST DURABLE

Timberland PRO Men’s 26078 Titan 6”

Timberland PRO Men’s Titan Waterproof 6″ Alloy Safety Toe

  • Durable
  • Comfortable and lightweight
  • Insulated
CHECK BEST PRICE
Read Full Review

MOST ROBUST

Timberland PRO Men’s Hyperion

Timberland PRO Men’s Hyperion Waterproof XL ST Work Boot

  • Non-skid treads
  • Robust
  • Quick-lace for easy slip-on/off
CHECK BEST PRICE
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BEST QUALITY

Timberland PRO Men’s 6”

Timberland PRO Men’s 6″ Resistor Composite-Toe Waterproof Work Boot

  • Waterproof
  • Durable and high quality
  • Stable
CHECK BEST PRICE
Read Full Review

MOST SUPPORTIVE

Timberland PRO Men’s Direct Attach Six-Inch

Timberland PRO Men’s Direct Attach Six-Inch Soft-Toe Boot

  • Warm and have excellent traction
  • Supportive
  • Lightweight
CHECK BEST PRICE
Read Full Review

MOST SECURE

Timberland Men’s Flume

Timberland Men’s Flume Waterproof Boot

  • Secure
  • Sturdy and supportive
  • Lightweight
CHECK BEST PRICE
Read Full Review

STYLISH

Timberland PRO Men’s Pitboss 6”

Timberland PRO Men’s 6″ Pit Boss Steel-Toe

  • Impressive arch support
  • Lightweight
  • Attractive
CHECK BEST PRICE
Read Full Review

BUDGET FRIENDLY

Timberland Men’s White Ledge

Timberland Men’s White Ledge Mid Waterproof Ankle Boot

  • Excellent traction and a perfect fit
  • Keeps you snug
  • Waterproof
CHECK BEST PRICE
Read Full Review

BEST CHOICE

Timberland PRO Men’s Boondock 6”

Timberland PRO Men’s Boondock 6″ Waterproof Non-Insulated Work Boot

  • Breathable
  • Affordable
  • Excellent traction

CHECK BEST PRICE

Read Full Review

MOST COMFORTABLE

Timberland PRO Men’s Gravel Pit 10”

Timberland PRO Men’s Gravel Pit 10″ Steel Toe Waterproof Boot

  • Easy on/off
  • Lightweight and a perfect fit
  • Comfortable

CHECK BEST PRICE

Read Full Review

BEST TRACTION

Timberland PRO Men’s 52565 Endurance 6” PR

Timberland PRO Men’s 52562 Endurance 6″ PR Work Boot

  • Fashionable
  • Perfect fit
  • Incredible traction

CHECK BEST PRICE

Read Full Review

MOST DURABLE

Timberland PRO Men’s 26078 Titan 6”

Timberland PRO Men’s Titan Waterproof 6″ Alloy Safety Toe

  • Durable
  • Comfortable and lightweight
  • Insulated

CHECK BEST PRICE

Read Full Review

MOST ROBUST

Timberland PRO Men’s Hyperion

Timberland PRO Men’s Hyperion Waterproof XL ST Work Boot

  • Non-skid treads
  • Robust
  • Quick-lace for easy slip-on/off

CHECK BEST PRICE

Read Full Review

BEST QUALITY

Timberland PRO Men’s 6”

Timberland PRO Men’s 6″ Resistor Composite-Toe Waterproof Work Boot

  • Waterproof
  • Durable and high quality
  • Stable

CHECK BEST PRICE

Read Full Review

MOST SUPPORTIVE

Timberland PRO Men’s Direct Attach Six-Inch

Timberland PRO Men’s Direct Attach Six-Inch Soft-Toe Boot

  • Warm and have excellent traction
  • Supportive
  • Lightweight

CHECK BEST PRICE

Read Full Review

MOST SECURE

Timberland Men’s Flume

Timberland Men’s Flume Waterproof Boot

  • Secure
  • Sturdy and supportive
  • Lightweight

CHECK BEST PRICE

Read Full Review

STYLISH

Timberland PRO Men’s Pitboss 6”

Timberland PRO Men’s 6″ Pit Boss Steel-Toe

  • Impressive arch support
  • Lightweight
  • Attractive

CHECK BEST PRICE

Read Full Review

BUDGET FRIENDLY

Timberland Men’s White Ledge

Timberland Men’s White Ledge Mid Waterproof Ankle Boot

  • Excellent traction and a perfect fit
  • Keeps you snug
  • Waterproof

CHECK BEST PRICE

Read Full Review

The Top 10 Timberland Work Boots for Men Reviewed in Detail

BEST CHOICE

#01. Timberland PRO Men’s Boondock 6″ Waterproof Non-Insulated Work Boot

The work shoes have a sturdy leather upper and a breathable membrane that wicks away moisture. They also have a lightweight insulation to keep you warm and dry no matter how frigid the weather gets.

Timberland PRO Boondock

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We Like

They are the most supportive. They are also cozy, breathable, and robust. They also have excellent traction.

We Don’t Like

They are not as waterproof, and the heel breaks. Despite these issues though, they are a perfect fit, comfortable, supportive and breathable.

PROS

  • Breathable

  • Affordable

  • Excellent traction

  • Perfect fit

  • Sturdy ankle support

  • Tough leather skin

  • Roomy toe box

  • Super comfortable insert

CONS

  • Not as waterproof

  • Heel breaks

MOST COMFORTABLE

#02. Timberland PRO Men’s Gravel Pit 10″ Steel Toe Waterproof Boot

The sleek full-grain leather work boot offers your feet support and top-notch comfort. It has the Thermolite insulation and antimicrobial treatment lining which provide you with comfort and warmth; they also instantly wick away internal moisture and perspiration for a dry fit.

Timberland PRO Gravel

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We Like

It is the most comfortable work boot. It is also robust, lightweight, waterproof and insulated.

We Don’t Like

It is pricey, and the bottom detaches. Despite these shortcomings though, the work boot is sturdy, cozy and secure.

PROS

  • Easy on/off

  • Lightweight and a perfect fit

  • Waterproof

  • Comfortable

  • Stylish and warm

CONS

  • Sole detaches

  • Pricey

7 Steps to Choosing the Perfect Pair of Work Boots

BEST TRACTION

#03. Timberland PRO Men’s 52562 Endurance 6″ PR Work Boot

The Endurance Workboot redefines comfort by featuring the exclusive anti-fatigue technology which also absorbs shock and returns energy at key zones of your feet to deliver long-lasting, all-day comfort when you need it most.

Timberland PRO 52565

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We Like

It is the most fashionable workboot. It also gives you a perfect fit and excellent puncture resistance. It is also comfortable, affordable and the steel-toe cap provides you with supreme safety.

We Don’t Like

It is heavy, and the sole detaches. Despite these issues though, it is well-made and has excellent traction.

PROS

  • Fashionable

  • Perfect fit

  • Safe and cozy

  • Incredible traction

  • High puncture resistance

CONS

  • Bulky

  • Sole detaches

MOST DURABLE

#04. Timberland PRO Men’s Titan Waterproof 6″ Alloy Safety Toe

Their design is for hard-working service professionals. They provide you with lightweight, durable and safe boot for an extended period.

Timberland PRO 26078

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They have the TiTAN safety toe that protects you from heavy and hard falling objects, the PowerFitTM Comfort System for cushioning and the breathable, moisture-wicking air mesh lining to keep your feet warm and dry. The boots also boast of having the premium soft, full-grain leather for durability and the cement construction for flexibility thus minimising break-in-time.

We Like

They offer you the best fit. They are also secure, comfortable, durable, waterproof and lightweight.

We Don’t Like

The boots’ sole cracks and they have no ankle support. In spite of these minor issues though, they are cozy, secure and give you reliable slip-resistance.

PROS

  • Perfect fit

  • Durable

  • Comfortable and lightweight

  • Safe and breathable

  • Excellent arch support and traction

  • Insulated

CONS

  • Sole cracks

  • No ankle support

7 Steps to Choosing the Perfect Pair of Work Boots

MOST ROBUST

#05. Timberland PRO Men’s Hyperion Waterproof XL ST Work Boot

They make your days at the worksite comfortable and secure. They incorporate the alloy safety toe cap for superior protection and the lightweight molded EVA-midsole that offers you the much needed cushioning.

Timberland PRO Hyperion

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We Like

They are the most insulated. They are also lightweight, breathable, cozy, durable and slip-resistant.

We Don’t Like

They are not as waterproof, and they have no heel support. In spite of these issues though, the boots are cozy, sturdy and rugged.

PROS

  • Insulated

  • Robust

  • Non-skid treads

  • Snug

  • Lightweight

  • Quick-lace for easy slip-on/off

  • Breathable

CONS

  • Not as waterproof

  • No heel support

7 Steps to Choosing the Perfect Pair of Work Boots

BEST QUALITY

#06. Timberland PRO Men’s 6″ Resistor Composite-Toe Waterproof Work Boot

There’s no substitute for this heavenly, sturdy, guaranteed waterproof boot that keeps your feet cozy, dry, through either rain or sunshine. It has a rubber sole that provides you with excellent traction and Primaloft insulation for superior warmth and comfort.

Timberland PRO 6”

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We Like

It is the most durable work boot. It is waterproof, stylish and sufficient stability. It is also robust, warm and dry and has incredible traction.

We Don’t Like

It runs large and pricey. However, despite these few shortcomings, the boot is sturdy, cozy and durable.

PROS

  • Stable

  • Durable and high quality

  • Waterproof

  • Stylish and cute

  • Insulated

CONS

  • Pricey

  • Runs large

MOST SUPPORTIVE

#07. Timberland PRO Men’s Direct Attach Six-Inch Soft-Toe Boot

The Timberland sensational work boot has a mesh lining with anti-microbial treatment for odor control thus you can be confident even as you get them off your feet. It also has the steel safety-toe cap for safety.

Timberland PRO Direct

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We Like

They are the most lightweight Timberland work boot. They also have excellent traction and high insulation. They are also fairly-priced and supportive.

We Don’t Like

The soles fall apart, and they are not as waterproof as expected. However, they are lightweight, warm and budget-friendly.

PROS

  • Lightweight

  • Fashionable

  • Supportive

  • Warm and have excellent traction

  • Budget-friendly

CONS

  • Sole falls apart

  • Not as waterproof

MOST SECURE

#08. Timberland Men’s Flume Waterproof Boot

It is what you need when you need to look your best. It has the removable EVA foam footbed for cushioning.

It also incorporates the fully gusseted tongue to keep dirt and debris out. It also boasts of an incredible rubber outsole for impressive traction capabilities.

Timberland Flume

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We Like

It is lightweight, very affordable, secure and supportive.

We Don’t Like

It is narrow, and the eye hooks come off quickly. However, these shortcomings are nothing compared to the lightness and supportive nature of this boot.

PROS

  • Lightweight

  • Affordable

  • Secure

  • Sturdy and supportive

CONS

  • Narrow

  • Eyehooks pop out

STYLISH

#09. Timberland PRO Men’s 6″ Pit Boss Steel-Toe

It helps eliminate foot pain even after long hours of hard work. It is for those that cherish memorable outdoor adventures and expeditions.

It has the removable sock liner that provides you with comfort and the aggressive treads that offer you unsurpassed traction. It also meets ANSI safety standards with the incredible safety toe box.

Timberland PRO Pitboss

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We Like

It has the best arch support, is lightweight and lovely. It is also a perfect fit, rigid and fashionable.

We Don’t Like

The work boot for men wears off quickly. It is also expensive. Despite these issues though, the boot is comfortable, has great arch support and secure.

PROS

  • Impressive arch support

  • Lightweight

  • Attractive

  • Perfect fit and stylish

  • Secure and comfortable

CONS

  • Wears off quickly

  • Pricey

BUDGET FRIENDLY

#10. Timberland Men’s White Ledge Mid Waterproof Ankle Boot

These pave the path to adventure, and it also helps you focus on the trail with its waterproof nature and incredible rubber outsole.

It also has a removable, dual-density EVA footbed that provides comfort and is perforated for additional air circulation. Be the master of your terrain today with this heaven-sent boot!

Timberland White

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We Like

It is a perfect fit and the best traction services. It also keeps you snug, is attractive, breathable, insulated and lightweight.

We Don’t Like

The eyelets pop off, and the sole detaches sometimes. Despite these matters though, the work boot is waterproof, breathable and has fantastic traction.

PROS

  • Excellent traction and a perfect fit

  • Keeps you snug

  • Waterproof

  • Attractive

  • Breathable

  • Lightweight

  • Insulated

CONS

  • Eyelets pop out

  • Sole detaches

Extra Mens Timberland Boots Options

Timberland Pro Direct Attach
weatherproof boots
Timberland Pro 6" Premium
Timberland White Ledge
Timberland Pro Flume
Timberland Pro 26078
timberland boots on sale
Timberland Pro Pitboss 6"

Choose The Perfect Pair in 2020

Video Review

You can see the demo for 2020 here

Common FAQ’s

Q: What Does ‘Break-in Period’ Mean?

A: When you buy work shoes they always tend to feel tight around the toes, rub your heels and pinch a little bit with every step at first. Since they are mostly products of leather, an organic material, they stretch as they adapt to your feet. That process is what people refer to as the break-in period.

However, even with it being a necessary step, the break-in time depends on one’s taste in style, sole, leather and personal preferences.

Q: What is a Puncture Resistant Plate?

A: A puncture-resistant plate is a safety feature in a work boot that provides you with unrequited underfoot protection. It is essential for those working in areas where they are prone to bottom hazards such as nails, needles, metal shards and other sharp objects. It is a standard feature in work boots of personnel working in steel manufacturing plants and recycling plants as well as most construction sites.

Q: What is the Difference Between A Shank and A Puncture Resistant Plate?

A: Puncture-resistant plates offer you underfoot safety in work environments where you are prone to hazards such as nails, metal shards and other possible sharp or dangerous items. Steel shanks, on the other hand, provide you with arch support in various workplaces such as logging, ladder climbing or working on railroad ballast.

Our Top Choices For Men’s Timberland Boots

When narrowing down the detailed list of the best styless, we looked into durability, comfort and support features. Sustainability features include the tight leathery skin that gives you a product that is long-lasting. Support features include steel shank that provides you with excellent stability.

Our favorite boot is the Timberland PRO Boondock 6”. It is the most lightweight work boot. It has the steel safety toe cap for safety. The boot also has a rugged rubber outsole that offers excellent traction. It also does support the arch and reduces foot fatigue.

Related Resources

Want to weigh you options first, before committing to a timberland work boots? check out our other timberland work boots guides.

James Blake

James Blake

James has made it his mission to find the best work boots on the market. He's passionate about matching the right workboot to the right application because different boots are a perfect fit for different uses.

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