James Blake
(Rated from 44 reviews)

Updated 07 August 2019 by James

Most Comfortable Work Boots

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

It’s REALLY hard to choose the most comfortable 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 comfortable work boot: comfort & breathability features, waterproof features, safety.

FOR MEN: The Red Wing Heritage Classic 6 Inch (On special until end August 2019) has all the listed qualities and features, just some of the many reasons they beat their competition hands down. Trevor, a professional tour guide, has been using them for over five years now and he has nothing but praises for these work shoes.

He loves the boots’thick sole that is perfectly contoured and goes ahead to offer him ample support from the heel to the toe. He also adores the Moc-toe boot featuring white traction tread rubber outsole that provides you with superior slip-resistance, the waterproof leather upper that keeps the boot water-resistant, and the Norwegian welt construction that adds strength and durability.

He’s vowed not to get a different model again and regrets all the time he wasted on sub-standard models.

Therefore, if you want work boots that have a stain and perspiration-resistant design, ones that have the Goodyear welt construction that offers you superior durability and a pair that complement your casual lifestyle, then make sure that you do not fall for the cheap knock-offs and get the Red Wing Heritage Classic 6 Inch from the leading supplier at the lowest price we’ve been able to find as of March 2019.

FOR WOMEN: The Under Armour Valsetz RTS (On special until end August 2019) has all the named features and that is why it beats its competition hands down. Tracy, a renowned hiker, has been using them for three years now and they are unlike any other pair of work boots she has ever had. They have become her most treasured items every time she goes on her hiking expeditions.

She loves how they feature the UA Clutch Fit Technology that wraps her ankle with a lightweight “second skin” for powerful support & incredible feel, their water-resistant upper that is perfect for all-weather, and their lightweight TPU shank that provides mid-foot support. She is also fond of the synthetic leather & textile upper with welded, abrasion-resistant film around the perimeter of the foot that keeps her firmly rooted on the ground no matter the surrounding circumstances.

She’s vowed never to purchase a different model and regrets any time she wasted on sub-standard models.

If you want work boots that have an anti-odor technology applied to molded Ortholite sock liner to prevent the growth of odor-causing microbes, a TPU toe cap for extra protection, and a low-profile rubber lug sole grips the ground without weighing you down, then make sure you do not fall for the cheap scams and get the Under Armour Valsetz RTS from the leading supplier at the best price we’ve been able to find as of March 2019.

We have recently added updates to this blog post to include a couple of latest releases that are popular currently. We hope that they will assist you in your journey to find the perfect one for your needs.

Most Comfortable Boots Options

Men's Most Comfortable Safety Boots

Thorogood 814 4200 American Heritage 6 Moc Toe

Well-rounded, great value

Affordable
Comfortable and excellent traction

Our top pick

most comfortable steel toe boots

Awesome value

Insulated
Excellent support

* On special until end August 2019

Women's Most Comfortable Safety Boots

Our top pick

most comfortable steel toe shoes

Well-rounded, great value

Lightweight
Warm and dry

* On special until end August 2019

Men’s shoes & women’s shoes differ so we’ve put together an in-depth buying guide on the best most comfortable work shoes for men and the best most comfortable boots for women. Read them now! You can also check our guide on non slip work shoes or our detailed article on the best boots for men & our overall best work boot reviews on mybestworkboots now.

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Select Your Type Of Most Comfortable Work Shoes

Use the quick find buttons below to scroll to the relevant section.

In the past, according to statistics, almost 40% of work boot companies focused on providing consumers with protective features, leaving aside comfort and support features.

Unfortunately, such situations caused workers to deal with footwear that did great on one aspect, protection, but bad in other essential elements for them, such as comfort and support

However, in spite of these challenges, there is always hope out there. Since June 2019, more advanced options have been in production to give you not only safety and durability in the workplace but also convenience; they give you comfort, breathability, support and even style. These are the ones that double up for work as well as for your casual activities.

Now:

With that in mind, it is no secret that getting into research on these new models can be tedious. That is why we decided to help you out by narrowing down the top ten most comfortable work boots in the market. By checking this guide out, we hope that you will have an easy time purchasing that perfect boot that will send chills running through your body.

Important New Models

7 STEPS TO CHOOSING THE PERFECT PAIR

Download your free guide ►

Run and Own the World Today With These To-Die-For Comfortable Work Boots

When you are busy making money moves, hustling and bustling in the streets, construction sites, industrial sites among other worksites, all you need is a reliable pair of work boots that complement your struggle. Ones that enable you to have a good time as you start and end your workday. No one needs shoes that give them painful blisters and a terrible headache.

Well, with a broad range cropping up each day, you might be confused on the kind of boot that would give you a long-lasting smile each day.

Lucky for you we conducted thorough research and tried to help you out by narrowing down the top ten most comfortable work boots. Our reviews give you honest buying advice that you can trust. We also do provide unbiased Ratings to help you choose the best for your needs.

Waterproof Work Boots

What Are They?

It is a boot that gives you comfort in a hazardous working environment. They have plushly padded collars, incredible mesh linings or even the famous EVA insert foot bed features. These features offer you excellent cushioning and keep you snug so you can carry out your daily duties without always worrying about your feet. They make you feel like you can jump over the moon.

How Do They Work?

They are a combination of comfort, safety, breathability, durability and support features. These have the incredible EVA foot bed that gives you a plush feel as you move around, the padded collars that mainly provide your ankles with extra support and coziness and the mesh lining that complements the breathable membrane to give you a fresh feel. They help make your working days and even outdoor adventures worthwhile.

Why You Should Trust Us

What Work Boot Features Did We Look At for the Best Comfortable Boots?

Well, we have established that choosing, let alone purchasing a boot can be a bit confusing especially if you do not know what you are looking for in one. When you also consider that there are a large number of incredibly good options on the market, it is definite that it can be hectic. That is why we ranked the best ten to help you choose your perfect fit.

Our guides are honest and sincere. We provide you with all the information you need. We have compiled their pros, cons, features, reviews, and rating.

So, while writing this guide, we took into account the many features to look out for when comparing different styles.

Important Unbiased Ratings

Comfort & Breathability for Work Boots

First of all, we looked into the comfort and breathability features like the removable, metatomical, dual density EVA comfort footbed, the mesh lining and the padded collar that go out of their way to give you first-class comfort. There is also the reliable breathable membrane that provides your feet with a fresh feel while also wicking away any internal moisture.

Support & Waterproof Boots

Secondly, we considered the support and waterproof features. These include the Under Armour’s UA Clutch Fit Technology that wraps the ankle with lightweight ‘second skin’ for robust support and the tight leather skin

Other Considerations

Other things considered are the safety, weight, price, and brand of the work boot.

Thus, if you are looking for top-rated options with great features, then you will want to check out our best ten guide.

Top 10 Mens Most Comfortable Boots

BEST CHOICE

Red Wing Heritage Men’s Classic Work 6 Inch

Red Wing Heritage Classic 6 Inch

  • Insulated
  • Durable and waterproof
  • Secure and easy to break in
CHECK BEST PRICE

MOST ATTRACTIVE

Thorogood American Heritage 6 Inch

Thorogood American Heritage 6 Inch

  • Waterproof
  • Comfortable and excellent traction
  • Attractive
CHECK BEST PRICE

MOST RELIABLE

Wolverine Men’s W04821 Buccaneer

Wolverine W04821 Buccaneer

  • Reliable and easy on/off
  • Robust and affordable
  • Perfect fit
CHECK BEST PRICE

SAFEST

Carhartt Men’s CMF6366 6 Inch

Carhartt CMF6366 6 Inch

  • Lightweight and attractive
  • Safest work boots
  • Holds up well
CHECK BEST PRICE

BEST TRACTION

Caterpillar Men’s Diagnostic

Caterpillar Diagnostic

  • Excellent arch support and traction
  • Attractive and insulated
  • Slip-resistant
CHECK BEST PRICE

BEST ARCH SUPPORT

Irish Setter Men’s 83608 6”

Irish Setter 83608 6”

  • Holds up robustly
  • Durable leather skin
  • Perfect fit and arch support
CHECK BEST PRICE

BEST INSULATED

Timberland PRO Men’s Direct Attach Six Inch

Timberland PRO Direct Attach Six Inch

  • Easy on/off
  • Lightweight and insulated
  • Stylish
CHECK BEST PRICE

STYLISH

Keen Utility Men’s Pittsburgh

Keen Utility Pittsburgh

  • Aggressive boot-treads for excellent traction
  • Incredible price range
  • Stylish and easy to maintain
CHECK BEST PRICE

MOST COMFORTABLE

Timberland PRO Men’s Pitboss 6”

Timberland PRO Pitboss 6”

  • Breathable and comfortable
  • Lightweight
  • Supportive and a perfect fit
CHECK BEST PRICE

BUDGET FRIENDLY

Smith & Wesson Breach 2_0 Men’s Tactical

Smith & Wesson Breach 2_0 Tactical

  • Budget-friendly
  • Solidly constructed
  • Excellent arch support
CHECK BEST PRICE

BEST CHOICE

Red Wing Heritage Men’s Classic Work 6 Inch

Red Wing Heritage Classic 6 Inch

  • Insulated
  • Durable and waterproof
  • Secure and easy to break in

CHECK BEST PRICE

MOST ATTRACTIVE

Thorogood American Heritage 6 Inch

Thorogood American Heritage 6 Inch

  • Waterproof
  • Comfortable and excellent traction
  • Attractive

CHECK BEST PRICE

MOST RELIABLE

Wolverine Men’s W04821 Buccaneer

Wolverine W04821 Buccaneer

  • Reliable and easy on/off
  • Robust and affordable
  • Perfect fit

CHECK BEST PRICE

SAFEST

Carhartt Men’s CMF6366 6 Inch

Carhartt CMF6366 6 Inch

  • Lightweight and attractive
  • Safest work boots
  • Holds up well

CHECK BEST PRICE

BEST TRACTION

Caterpillar Men’s Diagnostic

Caterpillar Diagnostic

  • Excellent arch support and traction
  • Attractive and insulated
  • Slip-resistant

CHECK BEST PRICE

BEST ARCH SUPPORT

Irish Setter Men’s 83608 6”

Irish Setter 83608 6”

  • Holds up robustly
  • Durable leather skin
  • Perfect fit and arch support

CHECK BEST PRICE

BEST INSULATED

Timberland PRO Men’s Direct Attach Six Inch

Timberland PRO Direct Attach Six Inch

  • Easy on/off
  • Lightweight and insulated
  • Stylish

CHECK BEST PRICE

STYLISH

Keen Utility Men’s Pittsburgh

Keen Utility Pittsburgh

  • Aggressive boot-treads for excellent traction
  • Incredible price range
  • Stylish and easy to maintain

CHECK BEST PRICE

MOST COMFORTABLE

Timberland PRO Men’s Pitboss 6”

Timberland PRO Pitboss 6”

  • Breathable and comfortable
  • Lightweight
  • Supportive and a perfect fit

CHECK BEST PRICE

BUDGET FRIENDLY

Smith & Wesson Breach 2_0 Men’s Tactical

Smith & Wesson Breach 2_0 Tactical

  • Budget-friendly
  • Solidly constructed
  • Excellent arch support

CHECK BEST PRICE

Top 10 Womens Most Comfortable Boots

BEST CHOICE

Under Armour Women’s Valsetz RTS

Under Armour Valsetz RTS

  • Comfortable and robust
  • Functional
  • Durable leather skin
CHECK BEST PRICE

EASY TO CLEAN

Wolverine Women’s Flood Hand 6”

Wolverine Flood Hand 6”

  • Easy to clean
  • Slip-resistant
  • Simple to put on and take off
CHECK BEST PRICE

BEST ARCH SUPPORT

MuckBoots Women’s Tack II Tall Equestrian

MuckBoots Tack II Tall Equestrian

  • Excellent arch support and traction
  • Breathable
  • Warm/dry
CHECK BEST PRICE

MOST SUPPORTIVE

Skechers for Work Women’s Workshire Peril

Skechers for Work Peril

  • Stylish and durable
  • Flexible and versatile
  • Supportive
CHECK BEST PRICE

FAIRLY PRICED

SLOGGERS Women’s Rain & Garden Boot

SLOGGERS Rain & Garden

  • Odor-free
  • Insulated
  • Moderately priced
CHECK BEST PRICE

MOST COMFORTABLE

Forever Women’s Ankle High Combat Hiking

Forever Ankle High Combat Hiking

  • Secure and easy to break in
  • Excellent support
  • Comfortable
CHECK BEST PRICE

GREAT SUPPORT

Skechers Performance Women’s On-the-Go Cozier Winter

Skechers Performance On-the-Go

  • Worth the money
  • Simple to pull on
  • Arch support
CHECK BEST PRICE

STYLISH

DailyShoes Women’s Military Lace Up Buckle Combat

DailyShoes Military Lace Up

  • Comfortable and breathable
  • Easy on/off
  • Cute design
CHECK BEST PRICE

MOST DURABLE

L-Run Women’s Waterproof Winter Boots

L-Run Winter

  • Comfortable to slip-on/off
  • Waterproof and durable
  • Perfect fit
CHECK BEST PRICE

BUDGET FRIENDLY

Sheepskin Lined Women’s Pink

Sheepskin Lined Pink

  • Incredible traction
  • Hold up well
  • Easy to clean
CHECK BEST PRICE

BEST CHOICE

Under Armour Women’s Valsetz RTS

Under Armour Valsetz RTS

  • Comfortable and robust
  • Functional
  • Durable leather skin

CHECK BEST PRICE

EASY TO CLEAN

Wolverine Women’s Flood Hand 6”

Wolverine Flood Hand 6”

  • Easy to clean
  • Slip-resistant
  • Simple to put on and take off

CHECK BEST PRICE

BEST ARCH SUPPORT

MuckBoots Women’s Tack II Tall Equestrian

MuckBoots Tack II Tall Equestrian

  • Excellent arch support and traction
  • Breathable
  • Warm/dry

CHECK BEST PRICE

MOST SUPPORTIVE

Skechers for Work Women’s Workshire Peril

Skechers for Work Peril

  • Stylish and durable
  • Flexible and versatile
  • Supportive

CHECK BEST PRICE

FAIRLY PRICED

SLOGGERS Women’s Rain & Garden Boot

SLOGGERS Rain & Garden

  • Odor-free
  • Insulated
  • Moderately priced

CHECK BEST PRICE

MOST COMFORTABLE

Forever Women’s Ankle High Combat Hiking

Forever Ankle High Combat Hiking

  • Secure and easy to break in
  • Excellent support
  • Comfortable

CHECK BEST PRICE

GREAT SUPPORT

Skechers Performance Women’s On-the-Go Cozier Winter

Skechers Performance On-the-Go

  • Worth the money
  • Simple to pull on
  • Arch support

CHECK BEST PRICE

STYLISH

DailyShoes Women’s Military Lace Up Buckle Combat

DailyShoes Military Lace Up

  • Comfortable and breathable
  • Easy on/off
  • Cute design

CHECK BEST PRICE

MOST DURABLE

L-Run Women’s Waterproof Winter Boots

L-Run Winter

  • Comfortable to slip-on/off
  • Waterproof and durable
  • Perfect fit

CHECK BEST PRICE

BUDGET FRIENDLY

Sheepskin Lined Women’s Pink

Sheepskin Lined Pink

  • Incredible traction
  • Hold up well
  • Easy to clean

CHECK BEST PRICE

Choose The Most Comfortable Work Boots in 2019

Video Review of The Best Comfortable Work Shoes

You can see the demo for 2019 here

Common FAQ’s for The Most Comfortable Boots for Working

Q: What Are the Characteristics of High-Quality Comfortable Work Shoes?

A: Comfort varies from one person to another. The best comfortable shoes, however, are supposed to fit appropriately, offer you adequate support, absorb shock, and distribute weight evenly on your leg. They fight painful and annoying foot concerns so that you can work all day without any discomfort.
Moreover, these work boots feature elements such as insoles and midsoles that provide cushioning support, footbeds with gel inserts and air bubbles make you feel like you snug and keep you insulated and the EVA midsoles that offer the right amount of flex, cushioning, and shock absorption.

Q: What Is the Most Comfortable Outsole Construction?

A: The Direct Attach is the snuggest outsole ever. It is a fusion of the sole to the fibers of the upper to offer you a robust and watertight bond. The construction also provides you with a more lightweight and flexible work boot without compromising its durability.

Q: How Does One Determine the Best Choice That Matches Their Needs?

A: You need first to determine what you will use the boots for whether it is for work or casual purposes. Secondly, check out your working environment requirements. Are you working indoors, outdoors, wet or dry areas, cold temperatures or mildly warm conditions? When you examine these two considerations, you will have a perfect idea of the style you need to purchase.

Quick Summary Of Comfortable Work Boots

A comfortable work boot is one that combines breathability, shock-absorption, safety and waterproof features to make an incredible reliable boot. They give you the confidence to head to the beach, mountain, city streets and snow adventures without worrying. They provide you with warmth while also keeping your toes and feet entirely fresh.

To come up with our favorites we considered the safety, breathability, support and of course comfort features. These include functions such as the steel toe/composite toe caps, the breathable membrane, the steel shank and the mesh lining and padded collar respectively.

Our Top Choices For Men’s Shoes

To come up with the detailed list we considered the breathability, support and protective features of each one.

Our top choice is the Keen Utility Men’s Pittsburgh Steel Toe Work Boots. It is the most comfortable work boot on the market right now. It has the removable, metatomical, dual density EVA comfort foot bed that offers you ample support. It also has the abrasive resistant tough-tech leather that keeps the boot sturdy and a breathable membrane that promotes airflow while still keeping your feet dry and fresh. It gives you excellent performance and convenience.

Our second favorite most comfortable work boot for men is the Irish Setter Men’s 83608 6” Steel Toe Work Boot. It offers you the perfect fit. The boot has a robust leather upper to make the safety shoe last as long as you would need it. It also has the padded collar that keeps your feet cushioned.

Our Top Choices For Women’s Shoes

Our favorite work boot is the Under Armour Women’s Valsetz RTS Workboot which is the most lightweight boot. It has the UA Clutch Fit Technology that wraps the ankle with a thin ‘second skin’ for robust support and a fantastic feel. It also has the TPU toe cap for extra protection. You can move around with much ease.

Our second favorite most comfortable work boot for women is the Sloggers Women’s Rain & Garden Boot with “All-Day-Comfort” Insole that enables you to quickly slip-on and off at whatever time you want. The boot also boasts of having massive duty lug treads that give you a sure-footed traction whether you are in mud, water or muck.