Short on time – Here’s the Bottom Line:

  1. Timberland PRO Men’s Boondock Comp-Toe Waterproof Work Boot (Laced)
  2. Ariat Men’s Workhog H2O Work Boots (Pull-on)
  3. Sneaker style’ lightweight, work shoes but still with composite or steel toes and water resistant.

I was in the market for a new pair of boots (my old ones have lasted 4 years). I wear boots everyday working on our family’s 400 acre farm and I’d go so far as to say I live in my boots. I have to spend somewhere between 10-12 hours a day in them. 

I actually sent back 3 pairs of boots (free of charge using Amazon’s ‘try before you buy’ service available to all Prime customers), so don’t waste your time or money with any boots not on this list.

What Every Good Pair Of Mens Work Boots MUST HAVE:

  • Super comfortable (the ability to insert extra soles too is a bonus), I cover a fair bit of ground when I’m working, mainly just walking, so comfort is top of my list; for a reason!
  • Waterproof – where I live we get rain – lots of rain; but I’m out in all weather, all times of day and all times of year. So if they aren’t waterproof, I’m not even touching them!
  • Steel toe caps (or composite) – hmm I like them for protection but I don’t like them if it makes the boot too heavy or affects the way I walk. So yes I prefer steel caps but not at the expense of making me walk like I’m wearing ‘moon boots’.
  • Lightweight – comes back to my previous point but ties in all the other points. I need a boot to be comfortable, much preferably leather, waterproof with steel toes BUT lightweight. Or as lightweight as possible. Think about it: to add some comfy sponge to the inner soles isn’t going to add weight but it will improve the comfort of the work boot. 
  • Slip resistant and great for working in winter when there is snow on the ground.

So I guess the ultimate waterproof comfortable waterproof work boot needs to hit all that criteria above and that puts it in the Goldilocks ‘sweet spot zone’. 

Well…I bought just that boot 6 months ago, here it is. 

(Before that though, here’s a little bit about me as I generally don’t review stuff until I’ve used it for about 12 months or longer. And I definitely don’t review shoes!!

B.S Work Boot Reviews

Yup you read that right, sorry if I’ve offended anyone but I’m calling BS, here’s why, I just googled searched it and read the first 3 reviews. 

All nonsense, I don’t think that the people writing these reviews have ever had these boots they recommend, seen these work boots in the flesh or even tried on a waterproof work boot. Seriously. 

I know this, because our staff have those exact same crappy boots – and hate them! 

So I’m writing this to dispel a few myths spread by ‘internet experts’ and hopefully save you a good few bucks (because some of these boots aren’t cheap!) and recommended something better – far better, for the same money or less! 


The Most Comfortable, Waterproof, Lightweight Work Boots for Men

Timberland PRO Men’s Boondock Comp-Toe Waterproof Work Boot

These are the best, most comfortable, lightweight, waterproof work boots you will ever try on. Timberland is a famous brand, so you can buy with confidence as everyone knows who they are and their reputation is at stake and luckily they really have delivered here with this work boot. 

They are available in either a 6” or 8” high boot. With different ‘toe types’ i.e composite, steel etc.

Timberland have nailed it here for these important reasons:


If you can’t afford it, who cares how comfortable they are, right? But you get what you pay for, let’s be honest. The old saying ‘buy cheap and you’ll buy twice’ springs to mind. 

But here’s the thing: these boots are NOT the most expensive in their class. Big tick in the box there then. They are actually 30 bucks cheaper on Amazon than the nearest rival the ‘KEEN Utility’.

(You don’t have to buy the ‘PRO’ version, there is a standard model. The reason I did, is because if you’re in boots all damn day like I am, the PRO version are SERIOUSLY worth the few extra bucks – i’ll come onto why in just a minute.) 

The Boondocks are also roughly the same price on Amazon as the ‘Carhartt Rugged Flex’. Full disclaimer, whilst I haven’t tried one on, the reviews on Amazon aren’t as good as the Timberlands and they have less of them (by thousands). That’s proof enough for me. 


Walking around in boots all day can get so tiring but these don’t feel that heavy at all. In fact I couldn’t find the weight of the boot online so I weighed mine as a comparison. Admittedly they were still in the box with packaging etc but weighed just 2.9lbs (1.3kg). Come on, that’s like having a few cupcakes on each foot…

The point is, if boots are lightweight you can do more in them and don’t get tired as easily especially with the anti-fatigue soles. 

I’ll come onto the ‘anti fatigue’ feature of these boots in more depth in a minute, because when I read that I thought it was a ‘gimmick’. It really isn’t! 

Leather: Why Buy Leather Work Boots?

These boots are leather and you have to love leather for a few simple reasons:

Leather is waterproof!

It’s lightweight too, which ties into the point above, helping cut weight will mean I have more energy to do more stuff in them.

Breathability – again it’s that goldilocks zone, not too hot and not too cold. (Your socks actually have a large part to play in this too. So don’t blame the boots if your socks are synthetic too thick/thin or just not right for your work boot.) Leather is naturally breathable, which allows your feet to stay at the right temperature but with their waterproof integrity remaining.

Flexing – leather is malleable so it will flex just enough and then hold that shape around your feet. This is the reason that the old pair of boots you have are so comfortable, they have molded to the shape of your foot perfectly. Well made leather boots will do exactly the same thing. This boot will mold round your feet and provide the most comfortable work boot you have ever had.  

Hard Wearing – leather is very strong and as such is really hard wearing. A well made pair of Timberland boots could last you decades. 


Not water resistant, actually waterproof, like properly waterproof! Water resistant won’t cut it if you’re in boots everyday because slowly that resistance wears off leaving you with wet socks and damp feet. Don’t compromise, you’ll regret it. 

You can spray these boots down to clean them – whilst wearing them and not feel a drop of water on your socks. 

Anti Fatigue Technology

Before you roll your eyes, at ‘technology’ dreamed up by a marketing department, hear me out because there is something about these boots I couldn’t put my finger on at first – zero feet or back pain!

They achieve this by having what they call a ‘Dual-density PU midsole with shock-absorbing technology’. 

I honestly don’t care what they call it, it works and it works really well. Having this type of sole in a waterproof work boot is a must. Whether you buy the Timberlands or not look for a boot with this in the sole. Honestly I can stand in these boots for ages and you don’t feel it in your back. 

Timberland vs KEEN Work Boots

And for any work boot aficionado’s out there – yes I did try on a pair of KEEN’s that ‘rival’ the Timberland Boondock’s but they aren’t as comfortable, were actually the same weight (seriously even the 6” high compared to the Timberland 8”) and were 30 bucks more! (check the Amazon price and reviews if you don’t believe me). More money for less boot? No thank you. 

Slip Resistant – Great For Winter & Snow!

What exactly is ‘slip resistance’ and why are these boots great for winter and snow? You can probably tell by now that I don’t take anything at face value, I try everything out and come to my own opinion!

It’s simple, in the sole of these boots are traction lugs. So these provide awesome grip on ice and in the snow. They are of course really well insulated, meaning you can work comfortably all day when there is snow on the ground and your feet won’t get cold. 


On a scale of 1/10 these boots score a 10. If you want nothing else other than a super comfortable pair of waterproof work boots, then look no further. I mean Timberland are ‘the name’ of boots you think of when someone says ‘boots’. They are famous all over the world. 

Ooo I nearly forgot

The other great point about these boots is they come in a ‘wide’ fit and in half sizes so these boots will fit you perfectly no matter the size or shape of your foot. I actually don’t have very wide feet but these boots still fit really nice and snug. 


  • The most famous boot brand makes the most comfortable waterproof, lightweight work boot ever…(hardly surprisingly) It’s not just me saying this, thousands of 5 star Amazon reviews attest to this. If you buy using Amazon Prime they have a ‘Try Before You Buy’ feature which is cool, with free delivery and free returns.
  • They are cheaper than the rival KEEN and the same price as the Carhartt’s but my guess is the Timberlands will outlast these other brands. Great for winter as they are nice and snug but remain breathable, with amazing grip on ice with anti slip soles that have traction lugs. Fully waterproof (not water resistant!) meaning no more wet socks and damp feet. 
  • They look cool too, I’ve not mentioned this point above as I’m not an instagrammer I’m a farmer! But nonetheless they do look and feel great. 
  • They are also really durable as you’d expect with Timberland’s but also lightweight. I weighed mine and in the box with packaging and they weighed just 2.9lbs. So only 1.4lbs per boot. (By comparison a loaf of bread weighs 1lb.)    
  • Last but not least the anti fatigue technology means you can wear these for 10+hrs a day and not get tired feet. But not only that in other boots you start to really feel it in your back as the day wears on. In the Timberland Boondock boots you get no backache. 


Not a fan of laced boots, well you’re in luck, I got just the alternative for you…

I couldn’t not mention Ariat boots as they are ace, really comfortable for that style of boot, super hard wearing so what I’ve done is divided this review up into 2 parts.

The Timberlands top the list as best work boots with laces. The Ariat top the list for the best ‘pull-on’ work boots. Both pairs of boots are waterproof, leather, great for cold weather and slip resistant and come with steel or compo toes.


Most Comfortable Lightweight ‘Pull-on’ Mens Work Boots That Are Waterproof!

Ariat Men’s Workhog Pull-on H2O Work Boots

As I said you can’t have a list about the best most comfortable work boots without Ariat featuring! 

Ok I’ve actually classed these boots as pull-on work boots, because technically they are and they have little leather handles on the side to help you pull them on and off. But I can nearly/pretty much slip into mine without the need for pulling. So they are almost a ‘slip-on’ work boot too! Perfect for anyone who’s indoors and outdoors and constantly taking off boots and then having to put them back on.

I mention that as one of the key things that put people off these boots is they think they are heavy, uncomfortable and a pain to get on and off. Couldn’t be further from the truth they are very comfortable and great for winter being nice and snug.

At 1.65lbs they are also a really lightweight work boot that wont leave you with aching feet or lower back ache. 

So if you are looking for a waterproof, leather pull on work boot then look further. Ariat has a HUGE range of work boots. Check out all the different styles on Amazon (the cheapest place we could find them) and you will be scrolling for rows and rows. Different sole types and lots of different leather patterns seriously make for one of the most comprehensive ranges of leather work boots ever designed!

The ‘Ariat Men’s Workhog Pull-on H2O Work Boots’ are one of the most popular work boots from their range, so for simplicity sake I’m going to go in depth into this boot. It’s also the boot ive had for over 5 years. They have become the kind of the ‘go to’ work boot for farmers and ranchers as they are brilliant for a variety of jobs. 

Whether that’s machinery work, dealing with livestock, construction, ‘lifting and shifting’ in warehouses, you name it these boots won’t let you down even in cold winters with their slip resistant soles. 

The boots come with a composite toe with an ASTM certification so you’re covered if that’s required in your line of work.

They also offer half sizes (.5) all the way up to size 11. Plus they also offer a ‘wide’ fit in every size up to size 13. So in my view they are a really well designed and thought out waterproof leather work boot. 

Remember with Leather Work Boots…

This isn’t a con or a drawback but I have to mention this point for transparency. The big selling point of these boots is that they are 100% leather. That means they are warm, ‘wear in’ nicely and are long lasting. We love that.

Here’s my point though: they are, even longer lasting, with some due care and attention to the leather. Leather is a natural product and after time and heavy use it can dry, crack or scuff etc. 

All of this is normal and nothing really to worry about, but just know that maybe one a year (or more) hit them with some cheap leather polish or waterproof boot spray. Just to keep them on the top of their game.

It’s only like replacing the oil in your vehicle and then that motor will then run and run. Work boots are no different. Especially if they get wet a lot through winter and warm during summer. Honestly a little bit of waterproofing spray or leather polish and this will double their lifespan. Work smarter not harder!

Alternative to the Ariat Men’s Workhog Pull-on H2O Work Boots

Slight curve ball but hardly as they are very similar in all respects. Timberland makes a few different pull on work boots in the similar style just with a different toe. 

So what I mean by that is they sell pull on’s with a composite toe, an alloy toe or a ‘soft toe’. A soft toe has no toe protection. Perfect then depending on your line of work and what you could be required to wear ‘toe wise’.

Price wise compared to the Ariats the Timberland’s are roughly the same price or maybe 20 bucks cheaper. There isn’t much in it. 

But the Timberland Pull-on’s are all part of their PRO range meaning you get the anti fatigue technology in the soles which makes all the difference. And Timberland work boots are famous for being waterproof, comfortable, lightweight and of course super hard wearing.

Hey it isn’t my money you spend it how you wish – pick the boot that’s best for you!

Sneaker Work Boot/Shoe 

If you’re not required to do any really heavy work and therefore don’t really need boots or could get away without, sneakers make a great option. Hear me out before rolling your eyes.

Sneaker style work boots are really popular because they are comfortable, super lightweight, water resistant (some are fully waterproof) and can come with steel toes or composite toes! 

I mean, bear in mind these sneaker type work boots won’t last as long as the ‘proper’ work boots mentioned above like the Timberland Doondock’s or the Ariat WorkHog’s. But if your work doesn’t require you to have a ‘proper’ boot but still have toe protection then sneaker work shoes are a great option, especially in summer. They are breathable and lightweight, what’s not to like.

Comfortable work boot sneaker brands to look for are:

There are a whole bunch of ‘work sneakers’ on Amazon that are unbranded and I’m guessing imported from China. No bad thing though. They are also fairly cheap but I don’t know if these are any good so I’m not recommending them. But if you’ve bought a cheap pair and like them and they lasted, stick a comment in the comment sections below to help everyone else out.  

Recap: The Most Comfortable, Lightweight, Waterproof Work Boots For Men

1. Timberland PRO Men’s Boondock Comp-Toe Waterproof Work Boot (LACED)

2. Ariat Men’s Workhog H2O Work Boots (Pull-on)