Strut your stuff in Timberland’s best work boots. Perfect for a long day on any job site, these boots provide the comfort, support, and protection you’ll definitely appreciate.
Timberland PRO Boondock
- Versatile and incredibly durable
- Rugged protection, solid construction
- Very comfortable for long hours on your feet
Timberland PRO Disruptor Oxford
- Look and feel like Vans/canvas sneakers
- Eye-catching casual style
- Fatigue-reducing design
Timberland PRO 6IN Direct Attach MaxTRAX
- Incredibly heavy-duty construction
- Steel toe and sturdy leather upper provide maximum protection
- Aggressive MaxTRAX tread is supremely grippy
Timberland PRO Powertrain Sport Alloy Toe
- Ample cushioning and support for fast-paced days
- Lightweight without sacrificing protection
- Great for light-duty tasks
Timberland Men's Gridworks Waterproof
- Waterproof, resilient to moisture damage
- Wedge sole offers extra padding and support
- Handsome good looks
Timberland PRO True Grit Pull-on
Most people see Timberland as a “style-first” boot brand. Not surprising, given how prevalent “Timbs” have become in urban fashion in the last couple of decades.
But before they were the “Air Jordans of boots,” Timberlands were built as hard-wearing work boots. Specifically, they were crafted in South Boston to be waterproof and resilient against the harsh winters in the Northeastern United States.
To this day, Timberland still produces a wide range of tough-and-rugged work-specific footwear that is more than worthy to rival brands like Danner, Ariat, Georgia Boot, and J.K. Boots.
Best Overall: Timberland PRO Boondock
In all my testing, I have yet to find an overall more reliable and versatile pair of Timberland boots than these.
The Boondocks feature a tough full-grain leather upper, a combination of Goodyear welt and cement heel construction, and a thermal plastic urethane sole that’s slip- and oil-resistant. They are waterproof and feature the signature Timberland Pro rubber toe cap for extra protection against impact and falling objects.
The rigid external heel cup does an impressive job of providing stability when I’m walking on uneven terrain or slanted roofs. Plus, the six-inch height offers excellent ankle support while still being low-cut enough to kneel and crouch comfortably.
Between the dual-density polyurethane midsole and thick polyurethane footbed, the Boondocks have all the cushioning I need to be comfortable for a long day on the job.
What I Like
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Versatile, great for everything from electrical work to roofing to flooring.
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Anti-fatigue PU footbed and dual-density midsole offer top-notch cushioning for my above-average frame.
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Waterproof and resilient against damage.
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A really tough, rugged look that I like.
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The combined cement heel and three-quarters Goodyear welt construction ensures they’ll last a long time.
What I Don’t Like
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The Boondocks are heavier than average. Heavy-duty, for sure, but the weight can wear on me after long hours.
What Other Reviewers Say
With more than 2,300 reviews and a 4.6 out of 5-star rating, it’s clear that users appreciate what Timberland is delivering in the Boondock boots.
Rave reviews highlight their all-day comfort, cushioning, and padding. Some users complained the toe box was a bit tight, while others found it too roomy for their narrow feet.
However, most reviewers praise the boots’ adequate fit, waterproof construction, and overall reliability.
The Verdict
The Boondocks are just an all-around great pair of boots that deliver on quality, versatility, and durability. They’ll serve you well on any job site or trade, making them the ideal work boots overall.
Best On A Budget: Timberland PRO Disruptor Oxford
I bought these as a present for my mechanic son, who has been wearing the same style of slip-on Vans for over ten years. After a week of using them, he came back with nothing but rave reviews about their style, comfort, and performance.
Don’t get me wrong: these shoes are light in every sense of the word.
The canvas upper won’t endure hard use, so you’re better off saving them for light-duty tasks. However, since they weigh so little, you’ll be very comfortable even over a 12-hour work shift.
The anti-fatigue footbed offers extra cushioning without making the shoes too heavy. Though there’s less arch support than I might like, my son appreciates the stripped-down design that suits his specific foot structure.
What I Like
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Look and feel like cloth-top sneakers but feature an alloy safety toe and EH-rating.
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The canvas upper has a sleek, stylish appearance that Vans lovers can appreciate.
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The rubber sole is grippy and offers great traction on wet or slippery terrain.
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Lightweight and easy to wear all day long.
What I Don’t Like
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My son had just one complaint about these shoes: they started out a little stiffer than he liked, and tended to rub against his pinky toes. However, the problem apparently went away once the canvas relaxed and stretched to accommodate his feet.
What Other Reviewers Say
Combing through reviews on the Disruptor Oxford work shoes, I can see why wearers appreciate them as much as my son does.
Despite the lightweight construction, the shoes earn a lot of appreciation for their solid protection. They’re a favorite of those who prefer stripped-down, minimalist footwear on the job.
Be warned: a few users found them uncomfortable during the week or two required to break them in, with pain points on the ankles and arches.
The Verdict
If you prefer a more casual style of footwear for your work day, the Timberland PRO Disruptor Oxfords may be just the thing for you. They’re sleek, slim, and wonderfully lightweight but still feature all the OSHA-required protection for any job site. Though not the longest-lasting or heaviest-duty shoes around, they deliver the quality and comfort you need.
Great Value: Timberland PRO 6IN Direct Attach MaxTRAX
For heavy-duty jobs when you absolutely need a steel-toe boot for maximum protection, I recommend the Timberland PRO 6IN Direct Attach MaxTRAXs.
In addition to a very tough steel safety toe, the Direct Attach boots have a slip- and oil-resistant TPU outsole, the highly aggressive MaxTRAX tread, and an ASTM F2413-18 M/I/C EH-compliant rating.
The eight-inch leather upper provides excellent ankle support and protection, so they’re my go to when I’m roofing, framing, or doing anything that involves nail guns (and erratically flying nails).
The upper is also waterproof, so I can wear them comfortably during the British Columbia rainy season. However, the inner mesh lining is both breathable and moisture-wicking to keep my feet from getting swampy and stinky after long work days.
Best of all, the Direct Attach boots feature Thermolite insulation that keeps out the winter chill and damp. I can wear them in all but sub-freezing temperatures.
What I Like
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Waterproofing, breathability, and integrated 200g Thermolite insulation makes them great three-and-a-half-season work boots.
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Very aggressive tread and high-traction TPU outsole keep my feet planted firmly on slippery, rocky, or uneven ground.
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Solid leather upper is puncture-resistant and resilient against scuffs and scratches.
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The Timberland PRO 24/7 comfort system provides excellent cushioning and arch support.
What I Don’t Like
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The boots are heavy, but that’s to be expected with steel-toed boots.
What Other Reviewers Say
There are more than 5,000 reviews and a 4.6-star rating on these Timberlands, with users praising their durability, protection, and suitability for heavy-duty tasks.
A few complained that the break-in time was longer than average, even for leather work boots.
However, once broken in, users rave about their all-day comfort. Also scoring high marks is the boots’ tread and traction, with one reviewer claiming, “I can walk on mopped floors without even risking slipping.”
The Verdict
If you want a heavier-duty—and just plain heavier—pair of steel-toed boots, I recommend the 6IN Direct Attach MaxTRAX. They offer uncompromising protection against on-the-job hazards, waterproofing against rain and damp, and even insulation against the winter. You can expect at least five years of daily use out of these bad boys. They just don’t quit.
Best Athletic Style: Timberland PRO Powertrain Sport Alloy Toe
When I came across the Timberland PRO Powertrain Sports, I was immediately intrigued.
A work boot built like a sports shoe? Yes, please.
The boot (more of a shoe, really) looks like my favorite running shoes, complete with a breathable mesh lining, anti-fatigue technology in the footbed and outsole, and low-profile versatility.
However, they’re still work-friendly thanks to the integrated alloy safety toe and slip-resistant outsole.
The ripstop nylon upper isn’t quite as tough as leather, but it can withstand “light-duty” jobs.
They’re the ideal lightweight work shoe if you’re moving fast and on your feet all day.
What I Like
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Incredibly lightweight—just a few ounces more than my favorite sport shoes.
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Breathable and comfortable even in the heat of summer.
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Solid cushioning that’s great for supporting my heavy frame.
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Low-cut and sleek. Highly versatile.
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Look like a sport shoe but feature all the requisite protection.
What I Don’t Like
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For all its durability, the ripstop nylon upper will never be quite as resilient as tough full-grain leather. I’ve been wearing mine for over a year, and the upper is already showing wear and tear, which tells me I’ll have to trade them out soon.
What Other Reviewers Say
The Powertrain Sports have amassed a breathtaking 17,500 reviews and still maintained a 4.5-star rating. Clearly, they’re doing something right that users are loving.
Positive reviews emphasize their durability (for synthetic shoes), minimal weight, work-friendly construction, and top-notch comfort.
A few reviews mention quality control issues with the sole in particular. A handful of wearers complained the sole split open after just a few months.
However, for the vast majority who didn’t encounter this problem, the Powertrain Sports’ outsole is praised for its slip-resistance, traction, stability, and support.
The Verdict
Through the Powertrain Sports, Timberland delivers the ideal work shoe I’ll usually wear when laying flooring, plumbing, or doing other “light-duty” electrical work. Their athletic design makes them exactly the lightweight, versatile, and ultra-comfortable shoes I like to wear during the heat of summer, too.
Best Waterproof: Timberland Men’s Gridworks Waterproof
There’s a lot I love about the Gridworks boots.
First, they’re made with a handsome premium-quality full-grade leather upper that combines durability and stylish good looks, just the way I like it
Second, the leather is treated with a waterproof membrane that not only keeps out water and damp, but also shields the leather from damage that could accelerate its decay.
The wedge sole provides amazing cushioning and support for my big, heavy frame, and the integrated PU footbed doubles down on the padding. In fact, the footbed is designed for both shock absorption and energy return, so I expend less energy with every step thanks to its springy texture.
To ensure they’re fully safe for any job site, they come with an alloy safety toe, slip-resistant (and very grippy) outsole, and electrical hazard protection.
What I Like
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The wedge sole is ideal for big, heavy guys like me who need extra support and cushioning.
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The impact-absorbing, energy-returning footbed makes the boots feel lighter and springier.
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Handsome good looks combined with durability and reliability.
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Suitable for working on rough terrain. The outsoles offer amazing traction even if the ground is oily, slippery, icy, or muddy.
What I Don’t Like
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Like all wedge sole boots, the sole may be prone to separating from the upper with hard use. I had to get mine resoled after just three years.
What Other Reviewers Say
A few users had minor issues with a lump formed by the tongue that rubs painfully against the ankle. However, this seems to be a problem exclusive to new boots.
Once broken in, the Gridworks boots score high marks on comfort, thanks to their thick footbed, cushioning outsole, and supportive midsole.
Reviewers also praise their snug fit, reliable waterproofing, and stability even on uneven ground (or, in one user’s case, unstable scaffolding).
The Verdict
If you’re working in mud, rain, and damp, the Gridworks Waterproof boots are a great pick. They’re tough enough to handle wet conditions without wearing down or losing their stylish good looks. And thanks to their thick footbed and wedge outsole, they’ll be comfortable even for heavier guys.
Best Pull On: Timberland PRO True Grit Pull-on
On days when I can’t be bothered with laces, the True Grit Pull-ons are my go-to work boot.
The six-inch shaft and half-inch heel remind me of my favorite cowboy roper boots, and they’re versatile enough for any job, from framing to flooring.
Despite their lack of laces, the fit is nice and snug, so I never feel like my feet or legs are sliding around inside the boots. The ExoSpine technology gives them a nice, sturdy structure and keeps them from sagging with frequent wear.
I love that they incorporate not just a composite safety toe but also an internal SKYDEX met guard, so my feet are protected when I’m working around heavy objects and potential hazards.
Best of all, they’re waterproof, breathable, odor-controlling, and moisture-wicking.
What I Like
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Warm in cold weather but cool in hot weather.
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Pull-on design is convenient and comfortable, but the shaft still has a nice structure that feels supportive and sturdy.
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Excellent shock absorption and impact reduction from the PU footbed.
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Very solid Goodyear welt construction. I’ve worn these for over three years, and they’re showing no sign of stopping.
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Thanks to the fiberglass shank integrated into the outsole, I’m very stable on uneven or rough terrain or on scaffolding, ladders, or roof beams.
What I Don’t Like
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I have to struggle a bit to slide my wider-than-average foot into the boots. Thankfully, sliding them out again is no hassle at all.
What Other Reviewers Say
The True Grit Pull-Ons are one of Timberland’s newer boot models, so few reviews are available.
In the negative reviews I could find, users found the same issue with pulling them on that I did, as well as the narrower fit for guys with wide feet.
However, most reviews were positive and praised the boots for their durability, comfort, and waterproofing. One user mentioned the outsoles’ resilience, saying, “I walk on fresh 300° asphalt all day, and the soles haven’t even started to separate.”
The Verdict
Timberland delivers quality, comfort, and performance in the True Grit Pull-ons, a pair of boots you’ll want to keep handy in your closet on the days you don’t want the hassle of tying and untying laces. Their tough safety toe and internal met guard make them ideal for high-hazard environments, and their structured upper provides the support you need for any job.
How to Choose the Best Timberlands for Work
Know the Difference Between Timberland and Timberland PRO
Timberland is the parent company, while Timberland PRO is the specific line of purpose-built work boots.
All Timberland boots feature enough insulation, traction, and waterproofing to make them useful for work. However, the Timberland PROs are explicitly constructed to protect you against the hazards and discomforts found on a long day’s work on a job site and thus are the right choice for professional tradesmen.
Choose The Right Timberland for Your Work Needs
You wouldn’t wear light-duty work shoes like the Disruptor Oxfords on high-hazard job sites, just like you wouldn’t wear heavy-duty Direct Attach MaxTRAX boots for a long day of hauling supplies across a job site.
Find the right boots (or shoes) for the specific work you’ll be doing. You can always upgrade or downsize down the line if your “dailies” don’t work for a one-off or short-term job.
Get The Right Size
As we’ve discovered, Timberlands and Timberland PROs both tend to run slightly larger.
Standard Timberlands will usually be a full size larger, while PROs are usually a half-size only.
What that means is that you need to buy a pair of Timberlands smaller than your usual size.
For example, if you’re normally an 11 ½ with other shoe brands, you’ll want to buy regular Timberlands in a 10 ½ or Timberland Pros in an 11.
However, pay attention to the reviews, because some (such as the Mt. Maddsens and White Ledges) do fit true-to-size.
Pay Attention to Certifications
The majority of Timberland PRO boots feature the necessary OSHA and MSHA safety features, including:
- Steel, alloy, or composite toe (though there will be some soft-toe shoes)
- ASTM F2413 rating for electrical hazards
- ASTM F2413 rating for oil- and slip-resistance
Standard Timberlands, however, may not feature any of these certifications.
If you’re working on a job site, you’ll want boots from the Timberland PRO line. However, if you’re just doing a DIY home improvement or renovation project, Timberlands not from the PRO line will be tough enough to protect you from most hazards.
Which Is Best for You?
Timberland has made its mark on the boot world by delivering eye-catching styles, industry-leading comfort, and long-lasting durability.
Their PRO line of boots delivers extra protection and work-specific construction that will be more than suitable for any job site.
Based on all my testing, I believe the Timberland PRO Boondocks to be the best overall. They’re versatile, sturdy, supportive, and look and feel exactly like what I’d expect from a top-notch pair of work boots.
However, if I’m going to be moving fast and working hard, the athletic style of the Powertrain Sport definitely holds a lot of appeal. Or, if you’re the kind of guy (like my son) who loves their slip-on Vans, the Disruptor Oxford hits all the right style notes while still offering ample protection.
For heavy-duty work, the steel toe and ultra-grippy rubber sole of the Direct Attach MaxTRAX is the right choice.
If you’re working around serious hazards and heavy objects that might fall on your feet, you’ll appreciate the double protection of the True Grits almost as much as the convenient pull-on design.
Finally, if you’re working in wet, muddy, or even icy conditions—or just want a pair of weatherproof work boots that offer extra comfort and cushioning—you can’t go wrong with the Gridworks Waterproofs.
