Most Comfortable Work Boots

Going to work is already hard enough to do. Your alarm goes off, it feels like only four hours has gone by since you’ve closed your eyes (and maybe that is the case), and then you have to drag yourself out of bed, shower, get dressed, and head off to work before the sun’s even up. The absolute last thing that you want to have to deal with is being uncomfortable all day due to poorly made or stiff boots. Don’t worry, we’ve got you covered.

We know the difference that having a comfortable, functional work boot can make – it make’s a world of difference. We spent hours searching high and low for the most comfortable work boots and we’re pretty sure we found the best of the best with this list. Any of these boots will make your work day go by fast and leave your feet feeling like gold at the end of the day. That being said, there’s still one that we think is the Most Comfortable Work Boot of 2017. Which pair could it be? Read on to find out!

Most Comfortable Work Boots 2018 – Comparison Table

Check out the table below first for a complete list of the most comfortable work boots and a couple of key features.

Timberland PRO Men’s Safety-Toe Work BootYes6”
Thorgood Men’s American HeritageNo6”
Red Wing Heritage Iron RangerNo6”
Wolverine Men's Mod-ToeNo6"
KEEN Utility Men's LouisvilleYes6"
Caterpillar Men's 2nd ShiftNo6"
Danner Men’s QuarryYes8”
Carhartt Men’s Composite Toe BootNo6"
Wolverine Men's Spencer BootYes6"
Timberland PRO Men's PitbossNo6"

Perfect! Now let’s take a look at the product reviews for each boot to figure out what the most comfortable work boots for men are.


Timberland PRO Men’s Safety-Toe Work Boot - Lightweight, Safe, and Comfortable

The first boot to make it onto our list comes from one of the most trusted brands when it comes to work boots, Timberland. Timberland is an American manufacturer that has been around since 1952 and while they will always be known for their classic work boot, they have expanded their footwear line to make boots that are more modern, lighter, more breathable, and overall are just adjusted for today’s society. The Timberland PRO Men’s Safety-Toe Work Boot is a perfect example of that. So what exactly about this Timberland makes it so comfortable?

This is your classic leather boot that features a rubber sole. The 6” measurement is referring to the length from the shaft to the arch, which is exactly how long this boot it. This is perfect if you need to get into tight spaces while you’re working. This is an ankle-high boot so it provides enough support and a great feature – it’s made from waterproof leather! It laces up in the front and inside features a proprietary PowerFit comfort system that will fit to any foot. The work tongue is contoured so it is not rigged whatsoever and also features a padded collar. While everything is very comfortable, you’re still going to want support. The Timberland PRO Men’s Safety-Toe Work Boot features a nylon diffusion shank that provides torsional rigidity, so your feet and ankles are still supported on the sides.

As far as safety goes – you’re going to be on the job so you want a boot that is going to keep you safe. You’re going to work, the last thing you want to do while you’re there is get injured. The rubber soles are abrasion, oil, and slip-resistant so you know you aren’t going anywhere. This boot also meets American Society for Testing and Materials (ASTM) standards for safety. IT features a TiTAN safety toe that’s actually 20% lighter than others, providing even more comfort.

Overall this is an extremely comfortable work boot. It has little to no break-in time and they basically start being comfortable right out of the box. It is very thoughtfully designed and has tons of features that take your comfort and safety into account. They also feature a mesh antimicrobial lining for odor control and ultimately even more comfort. For the price (around $150, depending on the exact version), it’s going to be difficult to beat how comfortable, light, and safe these boots are.

  • Toe 20% lighter than most
  • Waterproof
  • Little to no break-in time
  • Can be pricey depending on exact version purchased

Thorogood Men’s American Heritage - Industry Known Comfort

Timberland is probably the trendiest and most well known work boot out there. So much so that it’s even crossed over into streetwear a little bit, which some people might think give it a little less credence – but we won’t get into that in this article. However, just because a brand isn’t known by the masses doesn’t mean it’s not known in the industry and Thorgood is that brand. They’re extremely durable, trusted, reliable, American-made, and most importantly, they’re insanely comfortable.

This particular Thorogood is 6 inches high, made of leather and features a synthetic sole. It is an ankle length work boot and the toe is very stylish. It is not a steel toe like the previous Timberland, but it still protective depending on your exact industry. The material is soft, but not too soft as to not be protective so they provide maximum comfort. They offer a great fit and are very true to their size so no need to order up or down a size and are about medium width. Also since the leather is so soft, it feels as if the boots are already broken in. They’re essentially ready to wear right out of the box but may take a couple of days, depending on how broken in you like them.

It’s important to note that these boots are not waterproof right out of the box, however you can easily treat them to make them waterproof if you need them to be. One thing to note is that the sole is pretty thick so depending on your feet, they might be pretty close to the top of the shoe. This could be a personal preference, however. If you want a little more room, you can quickly and cheaply switch out the sole for something a little bit thinner.

Thorogood is an extremely reliable brand when it comes to work boots. They look great, they perform great, and of course the most important factor that we’re looking for is that they are extremely extremely comfortable. Depending on what color and size you choose, these will probably run you somewhere around $175, which is actually a decent price. Some boots that are this comfortable can easily run you double that. We can’t recommend these Thorogood Men’s American Heritage boots enough. These are definitely some of the most comfortable work boots for men. Right out of the box, we can guarantee you’ll have a more comfortable work day.

  • Ready to wear out of the box
  • Soft leather
  • Great price
  • Not steel toe

Red Wing Heritage Iron Ranger - Functional and Stylish

Here we have one of the most classic, reliable names in not just work boots – but specifically comfortable work boots. Red Wing has long been known for producing extremely comfortable boots that are not only great for work, but are also stylish enough to wear outside of work. Also a great bonus – they’ll make you one inch taller!

Meaning that the heel is approximately one inch in height, which is a nice little bonus. The shoe itself is made up of leather with a synthetic sole and a beautifully stitched cap toe. In addition to being extremely comfortable, we have to say that this might be the most stylish boot on our list as well. We love how it looks. It comes in a bunch of different colors so you can find one that works for you and we also love the contrast stitching all along the edges. It really makes them stand out and again, very wearable just about anywhere. A quick note however – you’ll definitely want to buy about a half size smaller than normal as the Red Wing Heritage Iron Ranger runs just a little bit big.

The sole of the boot is also non-marking so you won’t have to worry about it ruining any surface that you may be working on. They’re also oil resistant so no matter what the working environment, you’ll have a solid grip and won’t be slipping all over the place. While this boot is made with really nice leather, one down side of that is it will take a while to break in so don’t be discouraged if they are a bit uncomfortable at first – some of the best shoes are! Just stick it out and in no time, you’ll own some of the most comfortable boots you’ve ever put your feet in.

Overall, these are going to be tough work boots to beat. They’re comfortable, stylish, give you a little extra height, come in multiple different colors, and are pretty water resistant. They’re not technically “waterproof”, but they are able to withstand a fair amount of water which is usually essential when you’re working. We do have to mention that they are on the pricier side, depending on exactly what model you get ($200+) but we think they’re well worth the cost given their quality. While they may take a while to break in, we think the uncomfortable investment you’ll make in the beginning is more than worth how comfortable you’ll be for years to come in these boots.

  • Comes in multiple colors
  • Oil-resistant sole
  • Very stylish
  • Expensive
  • Takes a while to break in

Wolverine Men's Moc-Toe - Affordable With Extreme Comfort

Wolverine, another trusted name in the work boot world. But are the boots as powerful and tough as the name Wolverine suggests? For the Wolverine Men’s Moc-Toe we say yes! These boots are made tough and made to last while still maintaining an extremely high level of comfort. And one of the best parts of these boots? The price.

The Wolverine Men’s Moc-Toe might not be the most stylish on our list but that’s okay! These boots were made specifically to work in, and made specifically for manual labor at that so they are definitely made to last. They are made from high-quality leather and are moc-toe shoes so while they may not provide as much protection as steel-toe shoes, they still provide a little extra toughness around the toe. Alternatively, if you’re really after a steel-toe work boot, Wolverine actually makes this exact same shoe in a steel-toe alternative. Hooray!

Some additional features that helps skyrocket this boot to the top of the list of most comfortable work boots include a padded collar by the ankle so you won’t get sore from your ankle rubbing against it, a fully removable cushion footbed so you can keep it in when you want extra comfort or out when you want extra room to breathe, a springy rubber midsole, and also a nylon shank in the shoe that absorbs shock! So if you hit the ground hard a lot, it’ll help to absorb a lot of that pressure and make sure you’re fully comfortable throughout the day. The sole is also well traded so you won’t lose your grip no matter what surface you’re walking on. It’s also specially treated to resist oil, water, and abrasion so you can be confident you won’t go anywhere.

Alright, we said one of the best parts of this shoe is the price. And it is! This shoe, depending on exact size and model comes in at under $100 which is a great price for such a comfortable, durable work boot. Also unlike some of its competitors, the Wolverine Men’s Moc-Toe really doesn’t have a long breaking in period so after just a day or two, so you’ll be able to hit the ground running and it’ll feel like you’ve owned these boots for ages! Overall we think Wolverine manages to pack in a lot features to really make these comfortable work boots and at a great price point. If you’re looking for an affordable boot, that may not be the most stylish, but still offers durability and comfort – you can’t go wrong with the Wolverine Men’s Moc-Toe.

  • Great price
  • Little to no breaking in period
  • Padded collar
  • Not waterproof

KEEN Utility Men's Louisville - One of the Toughest

Everything about this KEEN boot screams work, durability, and traction. KEEN has long been a reliable brand name in work boots and specializes in a couple of things where other work boots sometimes lack: traction and water-resistance and the KEEN Utility Men’s Louisville boot is no exception. But sometimes with traction and water-resistance comes the sacrifice of comfort so do these boots live up to the comfort level of some of the other boots on our list? Let us find out.

Like just about all other work boots, these are made from high-quality leather and feature an exceptionally sturdy rubber sole. These boots, as you can probably tell from the photo, will not slip on anything. Ice, water, oil, you name it – you will be standing tall on both of your feet after walking across it all. The other main selling point of these boots is that they are waterproof! Most other boots offer some level of water-resistance but these are straight up waterproof. Even though they are waterproof, they’re still extremely breathable and you won’t have to worry about your feet heating up at all. They feature a thermoplastic polyurethane shank for mid foot support which is just fancy talk for plastic that’s specifically engineered to keep your feet cool, and support your arch. They’re extremely comfortable and offer exceptional arch support.

These utility boots are in fact steel toe boots so you’ll be protected in the most worrisome of circumstances. The steel toes are also asymmetrical so they fit more exact in both the left and right foot. They also feature locking metal lace hooks, which you might not think you need, but they’re great at keeping your laces in place especially through the elements and if they happen to get caught on things a lot.

These shoes are… tough. Very tough. A couple of down sides though – since they are so sturdy and tough they are going to take a little bit longer to break in than most other shoes. Give them a couple weeks, they’re very rigid. It’s also important to note that the KEEN Utility Men’s Louisville boots fit a bit wider than most so if you usually go for the wide version of a boot, you might not have to this time. These boots are also made partly from recycled material so they’re eco-friendly, which is always a nice bonus! If your number one priority in a boot, besides comfort, is protection – go for these. They’re waterproof but still breathable, feature a steel toe, and will prevent you from slipping on virtually any surface. They’re also moderately priced at just over $150 so you’re getting a pretty good value. Tough it out through the break in period and you’ll be rewarded with some of the best steel toe work boots for men that are ridiculously comfortable.

  • Very protective
  • Waterproof but breathable
  • Good grip
  • Take a long time to break in

Caterpillar Men's 2nd Shift - Inexpensive but High Quality

Caterpillar specializes in just about all things outdoors so when they have a work boot, we can be confident that we can trust it to be both tough and comfortable. And we were right because the Caterpillar Men’s 2nd Shift work boot is exactly that. At around $90, we were actually surprised at just how comfortable and sturdy these boots are.

Of course these boots are made of extremely high quality leather and feature a synthetic sole, as opposed to a rubber sole. Make note that these are indeed soft-toe shoes, not rubber shoes although that doesn’t affect its traction a whole lot. These boots come in standard as well as wide and while most boots do, it’s good to confirm that they do as not all boots will necessarily. They have a nylon sock liner and lining that’s very breathable and also very comfortable. They have an extremely durable welt construction and the synthetic sole has oil resistant traction which is always great to have. Speaking of the sole, it’s extremely thick and sturdy and almost impossible to puncture. So if you work in construction or in any other industry where there might be anything sharp laying around, these boots are great just in case you do happen to step on anything.

The Caterpillar Men’s 2nd shift also features a padded collar which is always helpful if you make a lot of lateral movements or are getting into a lot of tricky positions where your ankle is pressing up against your boot. You can be sure your ankle will be me with a nice soft material that won’t put any more pressure on than it has to. If you’re in need of a boot fast and don’t want to waste time with a long break in period, then look no further! These boots break in very easily and only get more comfortable as time goes on. After about a week, you’ll feel like you’re walking on air – these are seriously that comfortable.

If you’re looking for good value on a really comfortable boot, we highly recommend these. They’re well known for lasting an extremely long time so you won’t need to replace this for a long while. They come in three different colors and definitely aren’t the most stylish on the market, but are versatile enough to wear around outside of work. Don’t let the price fool you – these are extremely sturdy, comfortable, and like we said will last you for quite some time. We don’t think you’ll be disappointed with these Caterpillars, give them a go!

  • Great price
  • Break in very easily
  • Last a long time
  • Not waterproof

Danner Men's Quarry - Unbeatable Grip and Also Waterproof

It really seems that each work boot we feature manages to get sturdier, stronger, more comfortable, and more slip-resistant than the last! While Danner might not be as well known as some of the other brands on our list, that doesn’t mean it’s of any less quality. Danner has however, teamed up with a very well known brand Vibram to give some credibility to its sole. Find out what we mean.

First off you’ll be able to notice that this boot is taller than its counterparts on this list. While most are six inches high, this one is eight. Just those couple of extra inches gives it a more rugged look. They’re made of leather and if you notice the sole, it actually comes from Vibram! Vibram is well known for their slip-resistant soles they feature on other shoes and also on their own products. We’re not sure if you remember but they’re so slip-resistant, Vibram released “foot gloves” that were essentially just the soles of their shoes that were worn by athletes everywhere. Bottom line – they know how to make an extremely comfortable, and slip-resistant sole and we feel this really adds to the quality of the Danner Men’s Quarry boots.

Alright, enough about the soles – what about the actual boot? We’re glad you asked. These are 100% waterproof but still offer a lot of breathability. They’re triple stitched for extra durability and you can rest assured that these boots will be around for a long time. They also feature extremely rugged hardware to ensure that those laces will easily stay in place and keep your foot secure, adding even more to their comfort. Also for as rugged as they are, they have virtually no break in time and the fit is exactly what you expect, so no need to try and order a size up or down. Another great thing Danner offers is their customer support. They will redraft your boots (albeit for a fee) if need be, so you’ll never truly have to buy a brand new pair.

A couple of downsides to note. The laces themselves aren’t of the highest of quality so you might have to replace those fairly regularly – depending on the environment that you wear them in. They also aren’t very insulated so just be careful if you’re going to be working through the winter or in a cold environment. Easy fix to that one though – wool socks! Overall these are definitely top contenders for most comfortable work boots 2017 – they have an insanely comfortable insole so it’ll feel like you’re wearing work slippers after a while, the sole has an amazing grip, they’re completely waterproof, and on top of that they feature almost no break in period! These are expensive but like most expensive items on our lists, they are well worth the price. No disappointment found here in the Danner Men’s Quarry.

  • Amazing sole
  • Waterproof
  • Extremely comfortable insole
  • Not insulated, bad for the cold
  • On the expensive side

Carhartt Men’s Composite Toe Boot - Good for Bad Knees

Another top-of-the-line, extremely reliable, made-for-work brand name we all know and love – Carhartt! They’re known for specifically making warm, rugged outerwear that’s worn across all different industries across the country. While they might be more famous for their clothing, don’t dismiss their work boots! They have an extremely durable and of course, comfortable work boot – the Carhartt Men’s Composite Toe Boot and we think you’re going to love it.

This Carhartt boot is of course 100% leather and this time features a rubber sole. Another thing we love is that it’s only around $120. We think that’s a great price given such a high-profile brand name. Alright so a few features you’ll want to know about. They feature Rugged Flex which is actually unique to Carhartt. It’s essentially a proprietary technology that allows the material to move and stretch with you throughout the day so that whatever you’re doing, the material is moving with you and not just staying static. The rubber sole provides exceptional traction but is also shock absorbing! That goes a long way to alleviate pressure on the arch of your feet and also your knees. The sole is perfect for indoors or outdoors no matter what the surface is you’re walking on. On top of that, the sole is oil resistant and chemical resistant so you won’t slip nor will the sole be penetrated.

Adding to the comfort of these boots is the very generously padded tongue and collar to really cushion your feet in there. It truly and honestly feels like you’re walking on air and they also feature a very short break in period. While these shoes aren’t necessarily waterproof, they are fairly water resistant and should hold up to most everyday water encounters. They’re also very safe and meet all ASTM requirements.

Overall these are an extremely solid and comfortable pair of work boots that will fit just about everyone’s needs. They have a great proprietary Rugged Flex technology that we believe actually works, as well as a shock absorbing sole which is also very important. These shoes are especially good if you have bad knees as they provide a lot of support. So if you work in an especially harsh environment, have bad knees already, or just want to preemptively make sure you don’t get bad knees – check out the Carhartt Men’s Composite Toe Boot. Great comfort, extremely safe, and very affordable. You will not be disappointed.

  • Good price
  • Padded collar as well as tongue
  • Not 100% waterproof

Wolverine Men’s Spencer Boot - Lightweight and Breathable

Not surprisingly, we have another Wolverine boot sneak onto our most comfortable work boots list. Of course though, it’s for good reason. These boots not only look rugged and cool, but they also pack in a lot of features not seen on most other boots and they do so at a very reasonable price. Okay okay, so why did we decide to feature another pair of Wolverine boots on our list? You will find out in the next three paragraphs.

Unlike the others on our list, the Wolverine Men’s Spencer Boot is 90% leather and 10% nylon. This helps with creating a more lightweight boot as well as a more breathable boot. They are not steel toe but there is a protective toe guard that works just fine in most environments. These Wolverine’s also feature a removable cushion bed. We love that option because you get that extra comfort when you want it most, but you can give yourself a little room to breathe as well when you need it. Something else this features we haven’t seen in any other boot, is a moisture managing mesh line! This ensures that your feet won’t be sweaty throughout the day and won’t smell bad at the end of the day.

They also have cemented sole construction so you can be confident that they’re staying together. Speaking of the sole, these ones are rubber and have amazing tread on the bottom so you’ll be safe in the slipperiest of environments. These are also much much lighter than your typical work boot while still remaining sturdy. They have great ankle support and also feature a padded collar, which we think is vitally important. They also come in medium, wide, and extra wide so they’re able to accommodate the largest of feet.

We love these boots because they’re particularly breathable and also much lighter than your average work boot without sacrificing any support or safety. They come in a wide range of widths so they can be ordered to fit just about anybody – although we caution you order about a half size smaller than you normally would. They come in a few different colors, which is something we always love as well. The cushion bed is removable, and the moisture managing mesh line is something you’ll be hard pressed to find in any other work boot. For the price, these boots are hard to beat. If you’re looking for an affordable, lightweight, breathable work boot – look no further and pick yourself up a pair of the Wolverine Men’s Spencer Boot.

  • Extremely lightweight
  • Removable cushion bed
  • Moisture managing mesh line
  • Not steel toe
  • Not 100% waterproof

Timberland PRO Men’s Pitboss - Powerful and Comfortable

Alright and rounding off our list is another repeat brand -Timberland! These are the Timberland PRO Men’s Pitboss work boots and the boots are just as durable as the name is scary-sounding. Don’t let the name fool you, however! Just like the previous boots they are one of the more lightweight pairs that are featured on our list. So what did Timberland do with these boots to be able to score a second pair on our list of the most comfortable work boots? We’ll tell you!

These are 100% leather and like most others, feature a rubber sole. They really pay attention to the detail on these shoes though – they have great lacing hardware which goes a long way to make sure that your foot stays in place while you work. The leather is of extremely high quality and these boots will last you for years.

You can tell from the photo, but the toe is rounded and provides a lot of room and is also very soft to lessen any impact on your feet throughout the day. Another great feature is the removable sock liner that is also contoured for even more comfort! Again, we love the removable liner because when it’s in you get extreme comfort and when it’s out, you get breathability and you always have the choice!

If you work around electrics a lot, these boots also have electrical hazard protection to keep you safe from open circuits. They also look versatile so you’ll able to wear them at work and also outside of work. They come in multiple different colors so you’re able to customize them to your liking even further. Like we mentioned, they’re also on the lighter side so you’ll grow to forget you’re even wearing them over time. These are also true to size so don’t worry about any guesswork in ordering these – just order whatever size you normally would and you’ll be good to go. They do have a bit of a break-in period so don’t be discouraged when you first order them.

Overall, you can’t go wrong with this pair of Timberland PRO Men’t Pitboss. They’re lightweight, last a long time, have a removable cushioned insole, come in different colors, and have a slip-resistant sole. They’re extremely versatile and will fit the needs of just about anybody who purchases them. We love them and we know you will too.

  • Removable cushioned insert
  • Look is versatile
  • Electrical hazard protection
  • Not 100% waterproof

Most Comfortable Work Boots - Buyer's Guide

Like with any expensive purchase, you’ll want to make sure you take into consideration all of the important factors before just jumping in! Although you might think buying work boots is simple, there are still a lot of components you’ll want to take into consideration before buying! Okay so what are the important ones?


You’ll want to check the height of the boot first. The two most common ones are six inches and eight inches, with six inches being the more common of the two. This is almost completely a personal preference. Six inches will serve you for most purposes but eight inches do offer that little extra bit of support up above your ankles. If you make a lot of lateral or abnormal movements in your job, you might consider looking for an eight inch boot.

Steel Toe

Do you absolutely need a steel toe boot? While in some industries this might actually be the case, consider whether or not it’s actually necessary. A lot of steel boots are definitely comfortable but it’s much easier to find a comfortable boot that doesn’t have a steel toe. For that reason, we suggest that if you don’t absolutely need it in your industry, consider going for a softer toe.


Is this boot completely waterproof? Again, check and consider whether or not it’s absolutely necessary. A lot of completely waterproof boots are fairly breathable and can offer a lot of comfort, but ones that aren’t are generally lighter and a bit more breathable. Plus – most boots that aren’t necessarily “waterproof” are still water resistant and will still work for you in most scenarios.


If you are constantly working on slippery surfaces or just want boots that you won’t be slipping and sliding in, check out the sole. How is the tread? Is it rubber or synthetic? Is it oil resistant? Abrasion resistant? You’ll want to take a look at all of these factors.

Break-In Period

Did you just start a job and need to be in a new pair of work boots ASAP or do you have some time to break them in easily. This could be a big factor! Some boots take a while before they start being comfortable and are actually uncomfortable for the first few weeks. So if you want a pair where you can hit the ground running without any discomfort, make sure that they don’t have a long break-in period. However, if you still have a pair of boots that you can wear in the mean time while you slowly break in your new pair, consider going for one with a longer break-in period. In general, it’s usually worth the reward at the end.


We won’t lie, this was one of the tougher decisions that we’ve had to make on our lists! There were a lot of contenders for the most comfortable work boot 2017. We took a lot of factors into consideration – waterproof or not, break-in period, ultimate comfort, the quality of the sole, price, how long they last, versatility, and overall support. We wanted to find the most comfortable boot, but also one that offered some degree of safety and versatility and also recommend a boot that would work for just about everybody. With all of that being said and taken into consideration, we’re confident in our decision and think that we really have found the most comfortable work boot.

The boot that we are going to crown the winner on this list is….. drum roll….. the Red Wing Heritage Iron Ranger! It was a close race but we think this is a boot that can work for everybody. Its comfort is almost unmatched, it’s extremely water-resistant without the weight of being completely waterproof, the soles have a great tread, and they’re extremely versatile! You could wear these at work and head straight to dinner after if you needed to – all while remaining perfectly comfortable. And while they are one of the pricer pairs on the list, they are easily able to be resoled when they do need to be replaced so you won’t have to run out and buy a new pair when they do start to fall apart, although that will take a very long time. We love the Red Wings and they are definitely the most comfortable work boots for men. We can say with the utmost confidence that these will improve your work day and won’t leave you disappointed. Just remember to order about a half size smaller than normal and enjoy!