Timberland work boots run from a full size bigger than advertised down to a half size smaller. Unlike Timberland hiking boots, which run true to size, the work boot collection varies in size from model to model, and only a few styles run true to size. Depending on your location and boot selection, you may need to size between a half or full size up or down for Timberland work boots.
Shopping online for boots is awesome, right? It’s quick, easy, and convenient.
Well, it’s awesome right up until your order arrives and doesn’t fit. Then you have to check out how to get a refund, get a returns label, find time to ship it back, and you’re still without your boots.
It’s a bummer.
Timberland work boots such as the Pit Boss are a great example—they’re easy to buy online but notoriously hard to size correctly. Most Timberland boots need checking before you buy as their sizes vary a lot.
I’ve fallen into the “buy my usual size” trap before, and so to help you avoid making the same mistake, this guide will give you everything you need to know to buy the right size Timbs the first time.
Table of Contents
Do Timberland Boots Run Big or Small?
How do Timberland Work Boots Fit?
Timberland work boots tend to run on the big side, so it’s always better to err on the side of caution when buying them.
It’s worth distinguishing between a Timberland boot and a Timberland work boot, as most of Timberland’s hiking boots, sneaker boots, shoes, and Chukkas fit true to size.
The Timberland Pit Boss is one of the best soft-toe work boots around, offering comfort on top and protection below. With the classic Timberland look, it’s Ideal for working indoors where comfort and durability are needed.
A Timberland work boot needs a much closer inspection before you buy.
Buying Timberland work boots without trying them on first is like playing Russian Roulette with a double-barrel shotgun—you’re only right half of the time.
From a comfort perspective, Timberlands are great once you’ve got the correct size. Available in medium and wide fits, you shouldn’t feel constricted when wearing your work boots.
Depending on the type of boots you’re looking for, you’re either going to see a trend of boots that run too big or are true to size. Timberland’s Hiker boot selection is true to size, which would be great if you were on a site called HikerWearSpy.
Timberland offers some excellent work boots, including the iconic Timberland Premium 6” Waterproof Boot, which, like many of the work boot range, runs big.
Ah, the iconic design of the Timbs. Beyond being instantly recognizable, these are 100% waterproof and their Primaloft insulation make them an excellent rainy winter boot. The biggest downside is these are cemented sole construction rather than Goodyear welt, but you're getting style over longevity at this price point.
Location Matters
Your location might also have an impact—Timberland uses noticeable differences in the sizing for EU or UK buyers. A size 10 Timberland boot in the USA usually corresponds to an EU size 43, translating into a UK size 9.
Timberland advises that the UK size would actually be a 9.5, which means a buyer from the United Kingdom could buy a boot that’s a half size too large before they even think about Timberland’s running big anyway.
Timberland Knows About the Sizing Issue
It’s clear that Timberland knows that sizing their work boots is difficult. While most retailers have a section for customer reviews, Timberland has a sliding scale for each pair of boots that gives a size and fit estimate based on the reviews made by customers.
The more reviews, the better. It gives you a bigger picture of what to expect when sizing each boot. The Timberland Premium 6” Waterproof Boot matches my own experiences with this classic boot and shows a sliding scale that almost shouts that it’s a full size too big.
Aside from my experiences with Timberland boots, I’ve spent hours researching the brand’s most popular work boots to ensure the sizing you choose is as accurate as possible.
Not All Timberland Work Boots Run Large
Before you jump in and simply buy a size smaller than usual, it’s important to know that not all Timberland boots run big.
One of the most popular work boots in the range, the Direct Attach 6” Steel Toe Waterproof Work Boot runs on the small side.
The workhorse of the Timberland work boot line, the Direct Attach combines the looks you expect from a TImberland with the features you’d expect on the very best work boots. The Direct Attach keeps your feet dry and safe and, thanks to the additional padding, incredibly comfortable.
The Direct Attach is strikingly familiar, and it’s a lot like the classic Premium 6” Waterproof that Timberland built its reputation on. The Direct Attach is crafted from waterproof leather, has a breathable lining, and is oil and electrical hazard resistant.
While it’s similar to the Premium 6” Waterproof Boot, it’s a chunkier boot with a thicker, padded top collar, improving comfort when working in your boots all day.
Despite feeling and looking bulkier, its sizing is completely different from the Premium 6”.
The Direct Attach Waterproof Work Boot comes in half sizes, which is handy as it runs around a half size too small. If you’ve noticed half sizes feel tight on your feet, you’ll almost certainly have to go up a full size. Otherwise, you can easily get away with going up a half size.
You can buy the Timberland Direct Attach in medium and wide fit and in half sizes. Half sizes do stop at size 12, so you may have to go a whole size bigger for larger feet.
Timberland Premium 6” Waterproof Boot Sizing
No Timberland sizing guide would be complete without the Timberland Premium 6” Waterproof Boot. It’s one of the most recognizable work boots around, and it’s even commonly worn as part of a casual look rather than a work boot.
If it’s your first time buying this iconic boot, and you’ve been a size 9 for years, do yourself a favor and buy a size 8 or at least an 8.5. The fact that this style of Timberland runs up to a size too big is almost as well-known as the brand itself.
Despite not having the added functionality that the Direct Attach has, the Timberland Premium is built to last and feels incredibly comfortable to wear. The cemented outsole handles wet conditions well, even if it makes resoling often cost more than a new pair of Timberlands.
The Timberland Premium 6” Waterproof boot is available in medium and wide fit and comes in half sizes, so once you’re aware of the need to drop down a size, it’s easy to find the right fit.
Ah, the iconic design of the Timbs. Beyond being instantly recognizable, these are 100% waterproof and their Primaloft insulation make them an excellent rainy winter boot. The biggest downside is these are cemented sole construction rather than Goodyear welt, but you're getting style over longevity at this price point.
Timberland Sizes Can Be Misleading
The Timberland Pro Boondock Waterproof Work Boot is one of several 8” work boots that Timberland offers and is another example of a boot that runs between true to size and big.
If you’re looking for additional ankle support, the Boondock Waterproof Work Boot is an excellent choice. With an 8” shaft, the Boondock is roomy, waterproof, and perfect for those jobs that you can’t do without the additional support.
You should always check the size and fit of a pair of boots before buying, checking out the reviews to get an idea of what to expect. The reviews of the Boondock lean more towards true to size, but I’ve worn the Boondock myself and find it much roomier than stated.
Like all Timberlands, you can find Boondock boots in medium and wide fit and in half sizes, but it’s a big, bulky boot with a lot of room inside.
I would strongly suggest going down a half size if buying a pair of Boondock work boots—and you should consider them—they’re great boots, especially for working outdoors.
The width of the Boondock feels accurate. They’re not uncomfortable at all and have a composite toe and fiberglass shank that reduces their weight considerably.
True To Size Timberlands
One of the few Timberland work boots that are often true to size is the Timberland Gridworks 6” Alloy Toe Waterproof Work Boot, which comes in both medium and wide fit. The Timberland Gridwork boot also has an incredible size range, catering for feet as small as size 3.5 up to size 15.
Because they’re available in half sizes, you shouldn’t have any issue finding the perfect fit for these boots. The alloy safety toe feels light, and the Gridwork’s sole has a Goodyear welt, making a resole easy.
One of the smartest work boots around, the Timberland Gridworks could pass for a casual-wear boot. With an alloy toe cap and a steel shank, your feet are protected, even in the toughest conditions.
Despite being a wide boot, the Gridwork feels comfortable without being too tight or loose, and you’ll be able to buy your regular sneaker size without worrying.
Another hugely popular Timberland work boot is the Men’s Pit Boss 6” Work Boot, a great all-rounder boot that’s available in half sizes and medium and wide widths.
The Timberland Pit Boss is one of the best soft-toe work boots around, offering comfort on top and protection below. With the classic Timberland look, it’s Ideal for working indoors where comfort and durability are needed.
The Pit Boss isn’t ideal for heavy manual work but offers enough protection for those everyday jobs. You’ll find this boot is a perfect middle ground—it’s not too bulky, and its no-frills style gives you a lot of flexibility.
Like Goldilocks, you’ve got three choices. The Premium 6” Waterproof Boot runs too big, and the Direct Attach fits too small. The Pit Boss is a true-to-size fit, making it one of the easiest Timberland boots to buy.
Looking like a cross between a Roper boot and a Wellington, the Timberland True Grit Pull-On Work Boot is an excellent choice if you need extra calf protection from the elements.
The Western-themed True Grit boot is available in medium or wide fit, comes in half sizes, and has a similar sizing to most of Timberland’s Hiker boot range. It’s a true-to-size fit that feels comfortable from heel to toe.
The True Grit work boot has all the features you’d expect from a work boot, such as electrical hazard protection and safety toe, and offers serious waterproofing in harsh conditions.
Lightweight and sturdy, the TImberland True Grit Pull-On Work Boot looks amazing and feels even better. If you’re needing additional protection from the elements, this cowboy-inspired work boot covers all the angles. A true-to-size boot that’s easier to pull on than your slipper
I’ve found that this boot, while true to size, requires a bit of wearing in before it’s perfect. If you’ve ever worn cowboy boots before, you’ll know they can be one of the comfiest boots around once they’ve molded to your feet.
The True Grit work boot is the same—give them some time on your feet around the home, and they’ll feel like a second skin.
What If You Buy The Wrong Size?
If you’ve just bought a new pair of Timberlands and the size isn’t right, don’t stress. You’ve still got time to fix it.
Timberland boots come with a 30-day comfort guarantee, as well as pre-printed return labels enclosed with each order. Wear your new boots around the house for a few days, as you might just need to wear them in.
If it’s obvious that you’ve got the wrong size, return them and buy a size up or down, depending on how tight or loose they felt.
Timberland Boot Size Chart
I’ve added the Timberland sizing chart above with translations to UK and EU sizing. This chart reflects the sizing of their work boot line, which also includes the classic Timbs we all know and love.
The chart isn’t perfect, though—while it’ll help give you a better idea of the size you should get to fit the length of your foot, it doesn’t say much about the volume of your foot. It’s always a good idea to compare your boots to other brands, or to go try them on in person.
But if you’re in a hurry to get your new Timbs, then this chart should give you another helpful data point.
Size Really Does Matter
I’m a huge fan of Timberland work boots, especially the classic look of the Timberland Premium 6” Waterproof Boot. Despite that, I much prefer the Men’s Direct Attach 6” Steel Toe Waterproof Work Boot for its more complete protection while at work.
Sizing Timberland work boots can be a minefield if you’re unaware, but that’s why I wrote this guide—knowing there are pitfalls when buying the right size is half the battle won.
Ah, the iconic design of the Timbs. Beyond being instantly recognizable, these are 100% waterproof and their Primaloft insulation make them an excellent rainy winter boot. The biggest downside is these are cemented sole construction rather than Goodyear welt, but you're getting style over longevity at this price point.
With over 120 Timberland boots on offer, it’s impossible to size them all.
I’ve found several that are identical in all respects but the color and still found that one is true to size while the other has run big—so always check the size guide.
I hope you’ve found this Timberland sizing guide useful, and you should now know exactly what to look for when buying your next pair of Timberland work boots.
The workhorse of the Timberland work boot line, the Direct Attach combines the looks you expect from a TImberland with the features you’d expect on the very best work boots. The Direct Attach keeps your feet dry and safe and, thanks to the additional padding, incredibly comfortable.
FAQs
How are Timberlands supposed to fit?
Timberland boots are supposed to fit true to size, and while that’s the case for many of their ranges, Timberland work boots vary widely in size. Many of Timberland’s work boots fit large, except for the Direct Attach 6” Work boot, which runs a half size small.
Should you size up or down with Timberlands?
Many Timberland boots run big, so you’ll need to size down between a half or full size. The classic Premium 6” Work boot runs big by a full size, so you’ll have to drop down a size. Always check the reviews for each Timberland, as one size will vary from another.
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