I grew up in LA, but my very New England parents (both from Connecticut. Both Pats fans) made sure my siblings and I knew how to hunt and ride a horse.
Unsurprisingly, we were a religiously LL Bean family on the boot front.
It wasn’t until I tried my first Ariats a few years back, that I fell into a rabbit hole of exciting work boot options previously unknown to me in my boot bubble.
For one thing, I found pull-ons to be too much of a time saver to ever go back to laces.
So after plenty of research, here are my 6 best pull-on work boots for men. Whether you’re working on a construction site or farmland, I’m sure you’ll find the perfect pair for you here.
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6 Best Pull-on Work Boots in 2021
Most Comfortable: Ariat WorkHog
Ariat gave these an apt name. These waterproof work boots are tough. Combine that with Ariat's ATS comfort system, and suddenly working on your feet for 10-12 hours straight is much easier.
Ariat was founded in California by two Stanford brainiacs who applied athletic shoe technology to riding boots.
The WorkHog has a rugged cowboy look to it, complete with a stitched decorative pattern that’ll take you to any 1800s saloon in style. This pattern travels throughout the boot or just at the top depending on which version you opt for.
Because it’s designed to have an already rough look, maintenance is easy. Moreover, it’s as oiled and waxed as a South Dakotan’s pick-up truck.
The WorkHog features a unique cushioned EVA midsole, which is immediately comfortable and adaptable.
That being the case, the break-in period is more like that of an athletic shoe than a typical work boot. For some, the break-in period may even be non-existent.
What I Like
Sophisticated comfort technology
Very light for a work boot
Low maintenance
Great western riding style. This boot can be worn as a casual boot even off the field
What I Don’t Like
The WorkHog doesn’t have a proper steel toe. However, a lot of people like this quality because it makes the boot lighter without completely sacrificing protection.
What Other Reviewers Say
I’ve read several reviews written by workers raving about the WorkHog as a solution to their chronic ankle pain and policeman’s heel. The main complaint I’ve seen is the difficulty wide-footed individuals have fitting their foot through the shaft.
Overall, users overwhelmingly praise the boot’s comfort and easy maintenance.
The Verdict
The Ariat WorkHog is the best on the list for comfort. Look elsewhere if you need steel toes, but this boot is a durable, easy option with a stylish flare.
Ariat gave these an apt name. These waterproof work boots are tough. Combine that with Ariat's ATS comfort system, and suddenly working on your feet for 10-12 hours straight is much easier.
Best Waterproof: Irish Setter 83907 Wellington
The Irish Setter Wellington 83907 is a heritage work boot that doesn’t shy away from new techniques, one major highlight being its water protection technology.
Minnesota-based Red Wing Shoes introduced the Irish Setter line in 1905. The name came about because they were crafted from Red Russet leather, which has coloring similar to an Irish Setter dog (and immediately makes me biased because my childhood hunting dog was a Setter. RIP Mr. Jack, you OG).
The boot blew up in popularity among American workers in the 60’s. Red Wing shoes were also the main boot manufacturer for American soldiers during WWI, so they’re basically Ron Swanson approved.
As a brand, Irish Setter strikes a balance of embracing heritage-based tradition and practical new technology.
Wellingtons are waterproof, as a traditional hunting boot should be, but Irish Setter levels this up with a patented construction called UltraDry, a combination of full-grain waterproof leather and a moisture managed lining and Vibram sole.
The Irish Setter 83907 Wellington is easily the best waterproof boot on the list.
They’re also EH-rated, meaning they’ve been verified by the American Society of Testing and Materials to protect you from electrocution.
What I Like
Next-level waterproofing with its patented construction
Durable and long-lasting
Patented StableFlex technology for flexibility.
What I Don’t Like
They’re difficult to take on and off until broken in, and they’re still not that easy to take off even after being broken in
What Other Reviewers Say
Most of the online reviews come from workers like maintenance engineers and linemen who love the lifespan of the 83907 Wellington. There were a few complaints about the inside slipping from the boot at the heel making it difficult to take off, but the positive reviews far outweighed the negative.
The Verdict
The Irish Setter Wellington is a heritage work boot that doesn’t shy away from new techniques, one major highlight being its water protection technology.
The Irish Setter Wellington 83907 is a heritage work boot that doesn’t shy away from new techniques, one major highlight being its water protection technology.
Most Sturdy: Caterpillar Revolver
You can really beat this boot up like it stole your girlfriend. The Caterpillar Revolver is as tough as nails and great for ascending hikes.
You know a work boot can take a beating when a company that builds tractors makes it.
The Caterpillar Revolver checks off all of the work boot prerequisites: Steel-toed, rated by the ASTM, breathable, and ridiculously sturdy.
This may be one of the sturdiest work boots out there and is fitted with a steel shank. That plus a Polyurethane and Taibrelle sock liner keeps your foot cemented in place without compromising comfort and air circulation. They’re great for an uphill hike.
The Revolver’s outsole is carved with a deeply impressed tread pattern and is made of a tough rubber designed for maximum slip resistance.
The midsole is made of PVC, which adds another level of strength, abrasion resistance, and shock absorption.
And to really cinch this boot’s sturdy quality, it’s constructed with a Goodyear welt, which famously makes shoes easily re-soled.
What I Like
It’s a super tough boot that can really take a beating
Easy to slip in and out of, which is a huge time-saver
Simple design and silhouette makes it versatile
What I Don’t Like
Very narrow steel shank
What Other Reviewers Say
Users loved how strong the Revolver is. Many reviewers gave examples of the intense environments they subjected their boots to, including one guy who mentioned that water still couldn’t get in even when the stitching started to give out.
Regarding the narrow steel shank, users mentioned that this might not be the best boot for workers who spend a lot of time on ladders.
The Verdict
Feel free to really beat this boot up like it stole your girlfriend. The Caterpillar Revolver is as tough as nails and great for ascending hikes.
You can really beat this boot up like it stole your girlfriend. The Caterpillar Revolver is as tough as nails and great for ascending hikes.
Best on Concrete: Timberland PRO AG Boss
The Timberland PRO AG Boss is a true professional boot, designed for real-deal agriculture and livestock workers. It’s expensive, but definitely worth the money if you want as many of the latest work boot innovations stuffed into a fashionable, contemporary design.
There’s no denying that this brand is a cultural icon. After all, Timberland has a rapper named after it (whoah—I’m kidding, guys).
While most associate Timberland with the yellow boot that everyone was wearing to the club in the early aughts, the Pro AG Boss is a standout work boot—especially for hard floors.
It’s one of the best pull-on work boots for concrete floors because of its extra grippy sole and sophisticated cushion technology. The AG Boss has a patented Anti-Fatigue Technology, which not only absorbs shock, but also returns that energy to your foot.
The sole is dual density rubber with a low-profile lug so dirt isn’t picked up.
Style-wise, it’s a modern interpretation of an old Western work boot, with cleaner lines and a sleeker look. I also love the bright orange and black soles.
Other cool features include great temperature regulation that accommodates to changing environments, and resistance to blood-born pathogens.
What I Like
It’s an iconic brand that doesn’t coast on its reputation, this is a high-quality professional work boot
A lot of sophisticated extra features
Stylish and modern look
What I Don’t Like
Uncomfortable break-in period. This boot isn’t for the impatient
Expensive due to the name-brand popularity (thanks a lot, Timbaland)
What Other Reviewers Say
Upon scouring internet reviews, it seems that the Timberland PRO AG Boss has quite a loyal following. Despite the price tag, a lot of users will continuously replace their last Timberland PROs with new Timberlands PROs.
The Verdict
The Timberland PRO AG Boss is a true professional boot, designed for real-deal agriculture and livestock workers. It’s expensive, but definitely worth the money if you want as many of the latest work boot innovations stuffed into a fashionable, contemporary design.
The Timberland PRO AG Boss is a true professional boot, designed for real-deal agriculture and livestock workers. It’s expensive, but definitely worth the money if you want as many of the latest work boot innovations stuffed into a fashionable, contemporary design.
Best on a Budget: Ariat Groundbreaker
The Ariat Groundbreaker is our top entry-level work boot recommendation. If you’re on a budget or won’t be using your work boot too often or too seriously, this is your boot.
Ariat is so good, we gave them two spots in this roundup.
The Ariat Groundbreaker is a genuinely good work boot that also happens to be as affordable as it gets. Anything much cheaper than this is likely compromising a fundamental quality that makes work boots what they are.
Features include a rubber sole, removable insole, and a composition of 100% leather.
Before you even start to think that there’s nothing groundbreaking about this Groundbreaker, remember that you get all of these proper work boot features sometimes south of 100 bucks.
And in the grand tradition of Ariat, the Groundbreaker is a strong work boot with the comfort of an athletic shoe.
What I Like
Shockingly affordable
100% leather
Very comfortable
What I Don’t Like
While the Groundbreaker is long lasting enough, it has the shortest lifespan in this roundup depending on how hard you work it
What Other Reviewers Say
A lot of hobby farmers love this boot. This makes sense considering their low price point for a proper work boot. It seems they start to go after a year of hard work, but this didn’t offend most users.
The Verdict
The Ariat Groundbreaker is the entry-level option on this list. If you’re on a budget or won’t be using your work boot too often or too seriously like the hobby farmers above, this is your boot.
The Ariat Groundbreaker is our top entry-level work boot recommendation. If you’re on a budget or won’t be using your work boot too often or too seriously, this is your boot.
Best Steel Toe: Dr. Martens Icon 2295
If your workplace exposes your foot to a lot of falling objects, this is the work boot you want. Superior steel toe aside, the Icon 2295 is also fashionable and has come a long way since grunge kids rocked them in the 90s.
Iconic Dr. Martens need no introduction. A German doctor called Klaus Martens, the real-life Dr. Martens, founded the brand during WWII. He injured his ankle skiing and needed something more comfortable than standard army boots. The rest is history.
The Icon 2295 features all of the important work boot features, but it specifically gets my vote as one of the best steel toe work boots.
It’s heavy-duty construction and perfect fit combined with the steel toe makes this boot the best at preventing injuries from falling objects, toe injuries from slips, punctures, all of that.
It’s a bit on the heavy side, but the Dr. Martens Icon 2295 is the protector of the bunch. It’s like hiring presidential bodyguards for your foot.
Other features include an ASTM rating, water resistant tumbled leather uppers, durable air-cushioned PVC sole, and a fitted EVA foot bed.
What I Like
Very well fitted
Heavy construction for maximum protection
Ankle bone protector padding
What I Don’t Like
Like the Timberlands, this fancy guy is definitely on the more expensive side
What Other Reviewers Say
The reviews trend positive mainly due to the fit and level of protection. Users often give examples of the crazy heavy things that have fallen on their toe at work, and how the Icon 2295 made it so they lived to tell about it.
As far as the fit, reviewers often favorably compare these boots to other leading brands—Timberland and Red Wing get name-checked a lot.
The Verdict
If your workplace exposes your foot to a lot of falling objects, this is the work boot you want. Superior steel toe aside, the Icon 2295 is also fashionable and has come a long way since grunge kids rocked them in the 90s.
If your workplace exposes your foot to a lot of falling objects, this is the work boot you want. Superior steel toe aside, the Icon 2295 is also fashionable and has come a long way since grunge kids rocked them in the 90s.
Why Should You Choose Pull-on Work Boots?
Even if you don’t work in the field, pull-on work boots are ideal in wet or slippery situations and when you’re standing on hard floors for a long period of time.
They’re also effective for camping or other outdoor leisurely activities if you want to be stylish on top of practical.
When it comes to fashion, pull-on work boots range from utilitarian-chic to cowboy to clean contemporary.
Pull-on vs Lace-up Work Boots: What’s the Difference?
Pull-on work boots and lace-up work boots each have their pros and cons.
Pull-on boots save time, but with a lace-up, you can control and recalibrate the tightness and fit.
When it comes to safety, lace-up boots may offer stability and ankle protection, but their laces can come undone.
I’ve heard people say that lace-ups are better for outdoor work, while pull-ons are better for indoor work. This is a pretty quick-and-dirty analysis in my opinion.
Both are designed for safety and durability, so choosing between the two is a matter of preference, features, and style.
What Are the Common Characteristics of the Best Pull-on Work Boots?
All pull-on work boots offer strength and a level of comfort. Since they are utilitarian boots, it wouldn’t make sense if they were only durable but you couldn’t last an hour in them.
Each boot on this list effectively offers these qualities in a different way; the Irish Setter Wellington’s durability is based on its unique water-resistance technology, the Timberland PRO AG Boss’ comfort is about redistribution of energy.
Truly professional work boots tend to seek out accreditation, like an ASTM rating.
These Boots Were Made for Workin’
I hope you were able to find a work boot suited to your needs in this roundup.
After all, in this world there are workhorses and show ponies. All of the options on this list are unmistakably the former.
Ariat gave these an apt name. These waterproof work boots are tough. Combine that with Ariat's ATS comfort system, and suddenly working on your feet for 10-12 hours straight is much easier.
FAQs
How should pull-on work boots fit?
You should have an inch of room in front of your toe even as your foot moves, and your heel shouldn’t brush up against the back. There shouldn’t be pressure anywhere, but your sides should be secured.
How do you break in work boots fast?
Wear a new pair of work boots around the house for ten to twenty minutes a day to break them in quicker. Another good exercise is placing the middle part of the sole against the tread of a stair or a curb and rocking your foot back and forth.
What are the best pull-on square toe work boots?
The Ariat Workhog is available in a square-toed WorkHog variant that is as comfortable and durable as boots get.
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