The Most Comfortable Work Boots on the Market

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Anyone who works on their feet all day knows how vital it is to find the most comfortable work boots they possibly can.

Standing on your feet all day can be hell on your feet (not to mention your legs, back and the rest of your body), even when you’re wearing padded footwear.

And while work boots are usually pretty protective, a lot of models don’t provide nearly enough comfort or support for people who log a lot of long hours on the job site, like construction workers, cowboys and the thousands of other hard-working jobs in between.

The good new is that, when it comes to comfort, there are some work boots that (lame pun alert!) stand above the rest (you were warned).

In this post we’ve rounded up some of the most comfortable work boots on the market, so you can find the perfect pair to fit your job, your safety requirements and your style.

Work Hard, Walk Soft:

The Most Comfortable Work Boots for Men

Best Work Boots Overall↓
Danner Bull Run 6” Work Boot

Danner Bull Run 6” Work Boot

  • 4.5 Stars
    • 485 reviews
  • 100% Leather
  • Wedge Sole

Promising Review:

“Comfy right out the box. I’ve had boots that need to be broken in which can be a tough and uncomfortable task. These are great right away! Can’t wait till they conform to my feet. Worth the money.”

Check Price ➤


Timberland Pro Bosshog 6” Comp Toe Work Boots

Timberland Pro Bosshog 6” Comp Toe Work Boots

Timberland is one of the most trusted names in work boots on any construction site.

They’ve more or less got their manufacturing process down to a science, which is why you’ll see a few different Timberland boots on this list.

The Bosshog model features the company’s “anti-fatigue technology,” a polyurethane footbed that helps absorb shock and keep the boots feeling comfortable.


Ever Boots Tank Soft Toe Leather Work Boots

Ever Boots Tank Soft Toe Leather Work Boots

The Tank model from Ever Boots is not only one of the most comfortable pair of soft toe boots on the market, but also one of the sturdiest.

It features a comfortable leather sole and dependable goodyear welt construction, along with a PU insole to provide maximum comfort.


Keen Detroit XT Mid Boots

Keen Detroit XT Mid Boots

Keen’s Detroit model sports contoured underfoot support that’s designed to provide structured stability and comfort while still allowing for flexibility.

EH-rated, they have a leather sole and breathable waterproof membrane that keeps your feet dry and comfortable by letting vapor escape without letting water penetrate the boot.


Under Armour Men’s UA Valsetz RTS Tactical Boots

Under Armour Men's UA Valsetz RTS Tactical Boots

Long known for their comfortable and form-fitting clothes, Under Armour’s Valsetz boots feature the company’s “ClutchFit” technology, designed to contour comfortably around your ankle and feel so comfortable that it’s almost like a second skin, while still offering a powerful amount of support.

In addition, it sports Micro G foam that helps cushion your landings and a molded Ortholite sockliner with memory foam that provides maximum comfort.


Golden Fox 6″ Men’s Moc Toe Work Boots

Golden Fox 6" Men's Moc Toe Work Boots

Featuring a wedge sole and a polyurethane cushion insole, this pair from Golden Fox is designed to absorb shock and support both your legs and lower back, providing full comfort for long, hard days on your feet.

Goodyear welted and sturdy, they also have a rubber outsole that’s resistant to oil and chemical erosion, and provides good traction and support.


Wolverine Men’s I-90 Durashocks 6” Work Boot

Wolverine Men's I-90 Durashocks 6” Work Boot

Wolverine’s I-90 Durahsocks sport removable, dual-density polyurethane footbeds that make them extra comfy to slide your foot into.

And that’s in addition to the polyurethane midsole and the company’s Durashocks high-abrasion pads on the outsole, which offer maximum support.


The Most Comfortable Steel Toe Work Boots ↓

KEEN Utility Men’s Pittsburgh Steel Toe Work Boot

KEEN Utility Men’s Pittsburgh Steel Toe Work Boot

Another entry from Keen, their Pittsburgh boot sports asymmetrical 6″ steel toes, which means the steel toe cap is roomier and more comfortable than other models.

Like other Keen boots, this one’s also waterproof and boasts a breathable membrane liner that releases vapor while keeping water out.

In terms of safety features, these boots meet or exceed the following standards: ASTM F2412, F2413 I/75 and C/75 EH.

So they should be safe to wear around electrical hazards.


Timberland PRO 6” Pit Boss Steel Toe Boots

Timberland PRO 6” Pit Boss Steel Toe Boots

Timberland’s Pit Boss model is specifically designed with comfort and 24/7 wearability in mind.

Boasting the company’s “comfort suspension” technology and steel safety toes, the Pit Boss boots help to reduce foot fatigue, support your arches and provide maximum cushioning.

Stack all these important features on top of each other, and you get one of the best steel toe work boots for long days on the job site.


Skechers Men’s Burgin-Tarlac Industrial Boot

Skechers Men's Burgin-Tarlac Industrial Boot

Skechers has long been known for making comfortable shoes that you can wear all day.

So it’s no surprise that their work boots are among the most comfortable, too.

The Burgin-Tarlac model has a 5.5″ shaft, a rubber sole that provides good grip and support in a work environment with concrete floors, and memory foam that helps provide a comfy and supportive fit.


Caterpillar Second Shift Steel Toe Work Boot

Caterpillar Second Shift Steel Toe Work Boot

Though they’re certainly one of the best known and most trusted brands when it comes to industrial equipment, Caterpillar isn’t exactly known for comfort.

But it is known for being reliable and dependable, so it should come as no surprise that their ankle-cut Second Shift boots are comfortable, sturdy and, as the name implies, perfect for working two shifts in a row.


Thorogood Men’s American Heritage 6″ Moc Toe, MAXwear Wedge Safety Boots

Thorogood Men's American Heritage 6" Moc Toe, MAXwear Wedge Safety Boots

These are both one of the most comfortable work boots on the market and one of the best looking.

Thorogood’s American Heritage boasts goodyear storm welt construction and a removable shock-absorbing footbed that sits on top of its poron comfort cushion insole.

It comes in two colors, is made in the USA and boast slip-resistant outsoles made with high quality materials that offer electrical hazard protection.


The Most Comfortable Pull On Work Boots ↓

Irish Setter 83907 Wellington Work Boot

Irish Setter 83907 Wellington Work Boot

Irish Setter’s 83907 model combines the ease and waterproofness of a Wellington boot (e.g. a rain boot) with the safety and support of a work boot.

The insole features the company’s “StableFlex” technology, which provides a comfortable and stable fit, while the outside boasts waterproof full grain leather that helps keep your feet warm and dry, even in cold weather.

(And let’s be honest: few cultures have more experience keeping their feet dry than the Irish.)


Timberland PRO Ag Boss Pull-On Alloy Toe

Timberland PRO Ag Boss Pull-On Alloy Toe

Another entry from Timberland, the AG boss comes from their PRO line of safety footwear and is made of waterproof full-grain leather that will keep you feet dry and warm.

The boot runs 10″ tall from the sole up to the padded top collar, providing comfort and support not just for your feet, but well up the shins.


Ariat Men’s Workhog Pull-on Composite Toe Work Boot

Ariat Men's Workhog Pull-on Composite Toe Work Boot

One of the more Western-looking pull on work boots on this list, the Workhog model from Ariat comes with as much comfort as it does style.

At 10.25″ it’s slightly taller than the Timberland model listed above and comes with Ariat’s “ATS Max” shank (ATS stands for Advanced Torque Stability), which is designed to be lightweight and provide maximum comfort.


Dr. Martens Men’s Icon 2295

Dr. Martens Men’s Icon 2295

Best known (at least to people of a certain vintage) as the preferred boot maker of the ’90s grunge era, Doc Marten also makes some of the sturdiest and most comfortable work boots around.

Their Icon pull-on model comes with the easily recognizable air-cushioned outer sole that’s a staple of all Dr. Martens and resists oil, fat, petrol and alkali, while the upper boot is made from water-resistant, tumbled leather that will keep your feet and ankles feel warm, dry and comfy.


Wolverine Floorhand Waterproof Soft Toe Work Boots

Wolverine Floorhand Waterproof Soft Toe Work Boots

Also available in a steel toe model, Wolverine’s floorhand model is a little taller than some of the other pull-on entries on this list measuring 10.75″ from the sole up to the top of the boot opening.

But like many of the others it features a waterproof full-grain leather upper that will keep your feet nice and dry in wet conditions, and a slip-resistant rubber outsole that should help you keep a firm grip on the ground when navigating slippery surfaces.


Georgia Boot Men’s Carbo Tec-M

Georgia Boot Men's Carbo Tec-M

Like a lot of pull on work boots, the Carbo Tec-M from Georgia boots are designed for farm and ranch work.

They come with a comfort core insole that will help provide heel, back and arch support when you’re on your feet all day.

The boots are good year welted and boast Georgia’s waterproof system, which comes with the company’s 100% guarantee that air will get into the boot, but water won’t.


Caterpillar Men’s Revolver Pull-On Steel Toe Work Boot

Caterpillar Men's Revolver Pull-On Steel Toe Work Boot

Caterpillar’s steel toe Revolver boots are about as heavy duty as they come, but still manage to offer a lot of comfort and support.

In addition to the nylon mesh lining within the interior, the Revolver provides both comfort and customization:

It comes with both a polyurethane Taibrelle sock liner and a separate, removable polyurethane footbed, which you can combine as you see fit to find the right comfort level for your feet.

(Note that these also come in a soft toe model as well.)


Timberland PRO Powerwelt

Timberland PRO Powerwelt

Timberland’s Powerwelt pull-on model is a tough-as-hell Wellington boot.

It has an upper that’s made from 100% leather and a sole made from rubber.

The boot opening measures roughly 15″ around (making it wide enough to slide into even if you’re wearing thicker pants).

And it comes with the same comfort tech found in Timberland’s PRO line of comfortable work boots.


Golden Fox 12-Inch Wedge Pro

Golden Fox 12-Inch Wedge Pro

Another Wellington boot, this model from Golden Fox is much lighter than normal work boots thanks to the lightweight polyurethane wedge outsole.

The other major comfort feature is the dual density insole, which absorbs shock and supports both your lower back and legs.

In addition, the boots have a leather tab that makes it easy to slide them on and a traction pattern on the bottom that makes them easy to clean (which is especially helpful for farmers, ranchers or anyone who works in the mud).


Wolverine W04727

Wolverine W04727

Another Wolverine, the W04727 pull on work boot is an alternative to the Floorhand model listed above.

Featuring Goodyear welt construction, the W04727 has a removable cushion insole and comes fully unlined, making it more comfortable working in warm temperatures.

It has an upper made from Nubuck leather suede and hits roughly mid-calf and boasts a lightweight nylon shank that helps fight foot fatigue and get you through long days on the job.


Skechers Men’s Ruffneck

Skechers Men’s Ruffneck

Skecher’s pull-on entry into the comfortable work boot list features rubber soles that provide both comfort and grip.

It comes with removable insole, which helps you adjust both the size and the amount of padding in the boot itself.

It measures about 10.5″ in height from the arch of the sole up to the top of the boot opening, which is fairly generous at 14.5″ in circumference.


Georgia Boot Men’s Homeland G113

Georgia Boot Men’s Homeland G113

Made from 60% leather and 40% rubber, Georgia’s Homeland model mixes a rugged exterior with a padded interior.

It’s tough enough to keep the elements out but comfortable enough to keep your feet feeling supported.

It has a steel shank, an 11-inch height, and uses Georgia’s waterproof leathers to keep your feet dry as a bone.


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