Keen Pittsburgh
Hardware,  Home

Most Comfortable Work Boots 2020

Depending on the type of footwear, buyers’ priorities can vary quite a bit. Those looking for a pair of seasonal and stylish shoes may opt for something cheap that matches what they plan on wearing. For everyday use, something practical and inexpensive can do the job just fine. Work shoes? Something comfortable and reliable, flashy but not too flashy. For anything a bit more demanding, like crossfit or cold-weather wear, quality can become a big factor. But when it comes to work boots, comfort and durability are the big factors that buyers pay attention to. 

This is for a good reason: work boots have to take a lot of abuse and the wearer should ideally feel as little of that abuse as possible. Boots need to be comfortable, durable, and often need to provide protection from any number of dangers on the job site. A good pair of work boots will not only last a long time, they will make the work itself safer and leave the wearer less fatigued than they would otherwise be. Steel toe boots and composite toe boots protect against heavy items that may fall to the ground and injure the wearer, while other working people have to consider electrical hazards and slippery surfaces. So when we look at all of these factors, which boots still make the cut? Which boots are the most comfortable work boots? 

Caterpillar Second Shift: 


Caterpillar Second Shift


Starting this list off is a name that is well known to just about everyone who has ever walked by a construction site: Caterpillar. The Ubiquitous manufacturer construction equipment and heavy machinery also does a decent job of making work boots, and luckily they make boots in colors other than high-visibility yellow. They have a number of different models suited to various lines of work, but we have found that their best all-around pair is the Second Shift. 

The Second Shift Work Boot is a comfortable and breathable option that come in at a surprisingly low price point. Not only is the liner made with a mesh material to keep moisture and unpleasant smells at bay, the Climasphere insole itself is breathable. This means that these boots can keep your feet dryer for longer regardless of temperature. They are available in full grain leather among other finishes, are slip resistant,  and are available with both a soft toe and a steel toe. What really sells these for me is the Goodyear Welt construction, meaning these boots can be easily repaired with the sole wears out so you can use the boots for longer once they are broken in. 

Timberland Pro Pit Boss:


Timberland pro pit boss


Next up is a work boot from another well-known name: Timberland. In the past, Timberland has taken some flak in the past from those using their work boots for consistent manual labor have found them unable to stand up to the rigors involved. They are very popular as far as being fashionable goes, but are generally heavier and less durable than comparable boots. When you look at Timberland Pro boots, I suggest treating them like they come from another company entirely.

The Timberland Pro Pit Boss boots are a perfect example as to why. They are durable, comfortable, and pack a ton of great features into a boot that cost only slightly more than standard Timberland boots. The Pit Boss comes with a steel toe and a slip resistant sole rated for work on slippery and oily surfaces. They meet ANSI safety standards and are made with an insole that is antimicrobial, meaning that consistent moisture and drying won’t produce the same level of odor, if any. These boots also have a Goodyear Welt and cast metal hooks for the laces, meaning they will stand the test of time as well. 


Carhartt Rugged Flex:


Carhartt Rugged Flex


Carhartt is a name closely associated with workwear, but their boots are less well-known. Not that they are a small brand to any extent, it’s just worth pointing out that their coveralls, work pants, and jackets are very well known for their quality and durability. The work boots from their Rugged Flex line are no exception, and are the first boots on this list that are both fully waterproof and come with a composite toe. 

As their name states, the Carhartt Rugged Flex boots are meant for jobs that involve lots of ladder climbing and crouching, and put a huge emphasis on mobility while still being safe and durable. The waterproofing used is also breathable, meaning that unlike other waterproof work boots, these won’t leave your feet feeling like they spent the day in a sauna. The composite toe is complemented by the composite heel protections this boot offers, both made to meet regulated safety standards. The composite materials are much less conductive than their steel counterparts, meaning that these boots are rated for protection from electrical hazards of up to 18,000 volts. The cement construction of the sole may mean for a shorter overall lifespan, but it is more difficult to achieve proper waterproofing with a Goodyear Welt so this is an acceptable trade-off given the electrical safety standards these bring to the table. 


Keen Pittsburgh:


Keen Pittsburgh


Keen is a brand name that I have been seeing more and more when looking for work wear. They made their name producing high quality hiking shoes and other footwear made for the outdoors, so in a way, making work boots is the natural progression. Just take some light and sturdy boots, add a safety toe, beef them up a bit, and you’re good. They also take a fresh, modern approach to problems faced by consumers of work boots. They make most of their boots waterproof, for one thing, and they also make their boots as light as the materials allow for. The look is also more technical and in a way, more fun, meaning they are the best work boots for blending in for sure.

Make no mistake, the Keen Pittsburgh are still sturdy steel toe work boots. The sole is slip resistant on the outside, and the inside is made to contour to a wearer’s arch to provide maximum support. This can be crucial to those working long hours on their feet. These are waterproof work boots and are made with cement construction. The steel toes themselves are asymmetrical, so there’s more room and a more secure fit. They manage to be breathable as well, despite the waterproofing. If you haven’t considered Keen before, it is time to try a pair out.

Timberland Pro Stockdale:


Timberland Pro Stockdale


Another pick from Timberland Pro, the Stockdale boot is the only boot on this list with an alloy toe. Out of all the safety toe options, alloy is the least common but in many ways the best all-around. The advantage to a steel toe is the strength and flexibility under force that steel provides. Composite toes are lighter but can crack or break under extreme stress. Alloy toes are lighter and thinner than steel, so the Stockdale boot is lighter than it’s steel toe equivalents, and has a few more millimeters of space around the toe. Looking beyond the toe, there are plenty of neat features found on the Timberland Pro Stockdale.

They use Timberland’s Gripmax technology, which combines aggressive tread with oil resistance, slip resistance, and a non-marking sole. The full grain leather upper portion is fully waterproof as well. While they are waterproof, the breathable materials they are made of combined with a mesh lining prevent moisture from becoming a big issue. With the quality you are guaranteed to get from Timberland Pro, these boots are a very strong option overall.

Wolverine Raider:


Wolverine Raider


Wolverine boots have been around for quite some time and their excellent reputation stems from decades of manufacturing high quality footwear. The Raider is their flagship work boot and is a great combination of comfort and quality for anyone looking for a steel toe or soft toe work boot. They come in at a slightly higher price than the boots mentioned previously on this list, but are still a great value when you consider everything they offer. 

The sole is slip resistant and oil resistant, and the tread is aggressive enough to keep traction on rough surfaces as well. The mesh liner does a great job at managing moisture and the insole has a shock-absorbing material that makes working on hard surfaces like concrete much easier on knees and ankles. The insoles are removable so they can be dried easily when moisture builds up, which is also helpful if you use orthotic insoles for conditions like flat feet. The construction is interesting because Wolverine has their own ContourWelt technology that is like a hybrid of cement construction and a Goodyear Welt. The downside is that a Goodyear Welt makes boots almost universally repairable at shops that offer resoling. 


Irish Setter Farmington ​Boot:


Irish Setter Farmington


Irish Setter is owned by Red Wing, a manufacturer of premium boots known for their quality and durability. Irish Setter boots themselves are more work-oriented and utilitarian while Red Wing boots are american made and usually are a bit more stylized. The Farmington Boot from Irish setter is a dedicated steel toe work boot that is more focused on durability than style. That said, they are nice looking boots, and the spacious toe cap and reinforced sole make for a boot that can withstand abuse while sparing the wearer as much discomfort as possible.

These steel toe boots are ASTM rated for not only toe protection, but for electrical hazard protection as well. They have a removable insole so they can be dried easily. Some jobs benefit from padded insoles as well, so wearers are able to swap those in easily. They have a good slip resistance and oil resistance rating, and do an excellent job at resisting scuffing. With Goodyear Welt construction and a full grain leather upper, these boots can last years when maintained properly.

Thorogood American Heritage:


Thorogood American Heritage

Thorogood is an american manufacturer of heavy duty boots that manufacturers their products in the USA. They use high quality materials and make boots that can last decades when maintained. They come at a higher price point than the other boots on this list but are still a fantastic value when you consider what you get. Classic moc-toe styling in boots made of full grain leather. Put together by union workers with years of experience, the quality control that Thorogood practices is unmatched by competitors. This model boot is frequently the go-to answer to the question, “what is the most comfortable work boot?”

The American Heritage boot is available in steel toe and soft toe variants and both versions look incredible. The white wedge sole is attached via a Goodyear Welt and matches the white contrasting stitching that gives the boots a distinct and timeless look. The insole absorbs shock so you won’t feel fatigued as quickly on the job. They are also slip resistant. If you can swing the higher price tag, you will not be disappointed in the Thorogood American Heritage boot.

Red Wing Heritage Moc:


Red Wing Heritage Moc


Red Wing is a premium manufacturer of boots that are all made in America. They have an untouchable reputation for quality and durability, and made their mark making work boots since the 1950’s. These days, you are more likely to see Red Wing boots in a Brooklyn coffee shop than a construction site, due to their growing popularity as fashionable men’s boots. There is nothing wrong with a fashionable boots, and Red Wing products have never lessened in quality, they are still the durable work boots they have been for decades.

These boots do not come with a safety toe, and while the sole has great traction, they are not as slip resistant as more work-oriented boots. Still, for someone looking for a comfortable boot and work shoes, these are hard to beat. The sole is made to be supportive and comfortable inside and out, and the full grain leather is available in a number of different colors. Sturdy metal hardware and a good year welt come standard on all of Red Wing’s boots. These are a premium boot and the price reflects that, but if your work allows for a soft toe you should definitely try pair on. There is a good reason for the reputation that Red Wing has had for decades.

Chippewa Logger:


Chippewa Logger


Rounding off our top 10 is another premium boot made in America. Like Red Wing, Chippewa also has a great reputation that goes back decades. Unlike Red Wing, they still manufacture hardcore work boots that are regularly used in hazardous conditions. The logger boot is no exception to this. This is the only 8-inch boot on this list, but the height is necessary to the boot’s function. What makes this the best boot for logging is the aggressive tread and ankle support. The full grain leather upper of the boot protects your feet and ankles from branches and debris, and the steel toe protects the more vulnerable boots from falling branches and maybe the odd chainsaw.

The Goodyear welt and metal hardware ensure that these boots will be usable for years. While they look old school, the soles themselves are packed with modern features like a flexible and supportive insole and a Vibram outsole. These boots are also resistant to electrical hazards. Chippewa boots, while more expensive than some of their counterparts, are a great value when you consider all they offer and the fact that they are made right in the USA.

Buyer’s guide:

When shopping through the various boots available these days, the lists of features can seem daunting. Different types of construction produce boots with different qualities, and materials matter when it comes to performance and durability as well. Most of us are willing to pay extra for boots that will really do the job well, but it is tricky trying to figure out exactly which features really matter and which ones just sound nice on paper. Here are a few terms you may see when picking out a pair of boots:

Cement Construction:

Boots that use cement construction have a rubber cement attaching the sole to the upper portion of the boot. This is a more modern technique and allows boots to be manufactured lighter. Also, since there are no stitches passing between the sole and upper of the boot, most fully waterproof boots use this technique to avoid leaks. The downside is that, once the rubber cement attaching the sole of the boot to the upper begins to break down, there’s no easy way to effectively reattach the sole. They also generally can’t be resoled like boots with a Goodyear Welt can, hurting the longevity of boots with cement construction. If a boot’s construction method isn’t listed, then look at the sole itself. Usually boots made using cement construction have either no stitches visible or visible stitches that go directly into the boot, not vertically along the perimeter of the sole. 

Cement Construction

Goodyear Welt Construction:

A Goodyear Welt construction boot has the sole sewn onto the upper portion of the boot. This has several advantages: it can be used in accordance with adhesives to produce an extremely strong bond, it is very durable, and the sole can easily be removed once the outsole wears down so that a new sole can be attached, making a nice and broken in pair of boots feel nearly brand new. This means that a quality pair of boots can last years. While a Goodyear Welt is a bit old-school, many prefer this construction method due to the longevity of boots made using it. Look for soles with visible stitches on the perimeter of the sole. 

Goodyear Welt

Safety Toe Boots:

Safety toes are required for many jobs, and within the category of safety toe boots there is a good amount of variety. Safety toe boots can be broken down into three types:

Steel Toe Boots:

Safety toes are required for many jobs, and within the category of safety toe boots there is a good amount of variety. Safety toe boots can be broken down into three types: Steel toe boots have a crush proof toe box made out of steel that protects against harm from falling objects. This is useful to a number of workers who can face falling tools, building materials, and debris. Steel toe boots are heavier than their soft toe counterparts, and are more conductive therefore less ideal for electrical work. Many jobs require specifically steel toe boots that are rated based on workplace safety standards.

Composite Toe Boots:

Composite toe boots offer comparable protection to steel toe boots and are, on average, lighter and most resistant to electrical hazards. There are steel boots that are rated for electrical hazard, but they tend to be more conductive due to the metal inside the show. Composite toe boots offer protection from falling equipment and debris, and multiple fields of work allow for either composite toe or steel toe boots. One thing to note is that composite toes are very hard and durable, but don’t bend like steel when subjected to extreme forces. So some applications still require and old fashioned steel or alloy toe. If a workplace requires just any safety toe boot, consider composite toes for their light weight.

Alloy Toe Boots:

Alloy toe boots are less common than other types of safety toe boots, but are a nice choice in between a steel toe and a composite toe. Alloy toe boots are lighter than steel toe equivalents, and are often approved to wear in conditions that don’t permit a composite toe. The only downside is that lighter materials like aluminum tend to transfer heat and cold through the boot faster. So for hot conditions and cold weather, they may not be the best option.

Soft Toe Boots:

Soft toe boots have no protective toe box at all. Most boots are soft toe, and offer more protection to abrasion and impact than sneakers or casual shoes.

Six Inch vs. Eight Inch Boots:

In general, a 6-inch boot is what you need, minimum, for a work boot that provide protection to ankles and the lower shin. The higher the boot, the more support that goes to the ankle and the more protection that goes to the shins. Boots for welders, loggers, and other particularly hazardous trades tend to be higher for this reason. Bigger boots are obviously heavier and have slightly less mobility, so don’t go overboard with the height. Just get something that has adequate protection based on your needs.

Frequently Asked Questions:


Do I need waterproof boots?

Waterproof boots are great to have if you frequently work outdoors and in wet conditions. If you don’t generally come into contact with water where you work, it may be hard to justify the trade off with waterproof boots as they tend to be heavier and less breathable than boots that are not waterproof. Moisture is a boot’s biggest enemy, and breathability helps limits the moisture that builds up while the boots are worn, and more breathable boots dry faster once they are taken off.

What does a ANSI or ASTM rated mean?

ANSI and ASTM ratings are related to occupational safety laws that lay out exactly what a boot has to be able to endure to be suitable to certain work conditions. There are ratings for toe protection, electrical hazard protection, and puncture protection. Seeing these certifications is always a good thing and is required in many cases to be considered work appropriate in a number of occupations.

Do I need insulated boots?

If you work in very cold conditions (regularly below forty degrees Fahrenheit) then you should consider insulated boots. While these are less versatile than boots that aren’t insulated, as they are basically unwearable in warm temperatures, they can be invaluable in cold conditions. If you don’t work in the cold constantly, my suggestion would be to keep a pair of thick wool socks on hand with a backup in case the first pair gets sweaty, and trust those to keep you warm. If you, for instance, are a ski lift mechanic, then investing in insulated boots is a must. Thinsulate is a popular brand of insulation for work boots that is both warm and light weight, meaning you don’t have to walk around feeling like your feet are in concrete just because you’re outside in the winter.

How much do good work boots cost?

Generally speaking, it’s hard to find a good pair of work boots under $100. There are some on this list that go for less than that, and if you need specifically a mid-height soft or steel toe boot you have options at a reasonable price. If you need specialized boots or higher and more heavy duty boots for more hazardous tasks, prepare to pay upwards of $200. Good boots are an investment, and quality pays dividends. On top of the fact that higher quality boots get a lot more wear time, they also do a better job of protecting the wearer. When injuries mean missed work, good equipment is even more important.

What is maintenance for leather boots?

The biggest factor when it comes to work boot maintenance is cleaning. When boots are regularly cleaned, first with a damp cloth and then treated with leather cleaner, the exterior of the boots can dry properly and resist breaking down due to moisture. Gritty materials like mud can also tear away at the leather exterior of work boots. Oiling leather boots increases waterproofing and improves the life of the leather. Look for maintenance instructions from your specific boot manufacturer for a more in-depth idea of hat it takes to keep your boots going as long as possible.



There is a pair of work boots for every occasion, and you get what you pay for when it comes to quality. Consumers today enjoy the greatest selection of boots any generation of worker has had, and each year quality boots can be had for a lower price. A good pair can last years and provide comfort and safety to their wearer, and a bad pair can be something to complain about every day for months. Try on multiple pairs to see what fits. Try different sizes and widths available. Pair them with good socks and never let your feet or your boots stay moist for any prolonged amount of time. If you follow these simple guidelines, you won’t be disappointed.


Leave a Reply

Your email address will not be published.