Do Timberlands Run Big? Your Best Fit Guide

You’ve probably heard of Timberland boots and Timberland casual shoes; they’re one of the most incredible lines available on the market today. They offer durable and sturdy boots with an iconic look that work just as well for weekend camping on a mountain as they do if you’re more of an urban hiker walking on concrete.

However, choosing the perfect fit and size for you may have you wondering if what you see on screen is true to life. Do Timberlands run big, true to size, or smaller than other shoes you’re more familiar with?

Getting the right size can be easy if you remember that as a general rule, casual styles fit true to size, and Timberland boots like the Timberland Pro work boots run a half size to roughly a whole size bigger.

Whatever the style, read on to get the right Timberland fit and learn more about Timberland sizing.

How Do Timberland Boots Fit?

Finding your perfect Timberlands fit is as easy as measuring your feet, choosing the size using the chart on their website, and picking a style that works for you.

Timberlands are known for being comfortable and well-constructed, and many of their boots contain a MirrorFit system to help ensure that. This system consists of a midsole layer that remembers your foot’s contours from toe to ankle, like tracing your foot on a piece of paper. 

Certain styles of Timberlands run the same size as other brands, and thankfully, many different models of this iconic shoe are available to suit a variety of tastes. Knowing about each style will help you select sturdy work boots instead of more casual walking shoes. 

Are Timberland Boots Good for Wide Feet?

When determining the size of a boot, you determine the size number from more than just the length of the sole. The width of a shoe is also essential when finding the proper Timberland boots. 

When you try on shoes or estimate at home, remember that you should be able to move your foot by about an inch overall back and forth and from side to side while still fitting your foot comfortably. 

To give the most options for customers, most Timberlands come in medium or wide options, but they also offer some specialty sizes in their Timberland Pro and Pit Boss style of work boots.

One of the reasons that some styles of Timberland boots fit larger than others and are great for wide feet is their attention to outdoor needs. 

Hikers tend to need a Timberland boot for wide feet so they can fit thicker socks for heel and ankle support. 

Should You Break In Timberland Boots?

You should break in your Timberland boots, but it’s not going to be as quick as it is with thinner canvas shoes.

The nu-leather that makes Timberland boots long-lasting and durable also makes them a bit tighter and stiffer to wear at first.

Breaking in heavy-duty leather boots with thick rubber soles takes time, but using a few techniques, it doesn’t need to be painful or complex, and the result is worth it. 

Here are some tips for breaking in your Timberlands: 

  • Start slow and wear another pair of shoes while you break them in. This way, you can wear your Timberlands around the house for short sessions.
  • Wear thick wool socks or layer a few pairs of thinner socks to help stretch the leather and protect your heel from blisters.
  • Search for your pain points. Once you wear your Timberland boots a few times, you’ll quickly notice what parts feel too narrow, too big, or just don’t fit right.
  • Using a leather conditioner or even rubbing with just warm water, you can stretch and massage the fabric to a more flexible shoe for your foot.

The key is to have patience and take it one short session at a time.

Tips for Buying Perfectly Sized Boots

With the right size and style in mind, you’re now ready to find those Timberland boots that hug your foot. Here are a few tips to help ease that search.

Walk Up and Down an Incline

If you buy your shoes on Amazon or another shoe retailer website, walk up and down on an inclined street to make sure that your shoes fit properly before the return period ends. If you buy your shoes in a sporting goods store, they should have an inclined board for you to walk on.

Walking on an incline will help you quickly determine if your boots are too big and if your feet will slide around in them faster than walking on level ground will. 

Timberlands provide support and comfort, but if they are a size too big, the friction from the foot sliding around can cause a variety of problems, including:

These are all painful, unsightly sores, often near the side of the foot near the big toe but can occur anywhere that the fabric rubs. You don’t want any of them, trust me. 

Shop Later in the Day

Your feet are narrower when you wake up in the morning than when you go to bed because they experience a natural swelling as you move around throughout the day. 

So, when you’re shopping in-store or measuring on paper at home, it’s best not to shop for boots first thing in the morning to achieve an accurate fitting. 

Timberland Boots Sizing

If you want to know do Timberlands run big, you should first decide which Timberland boots style you would like. 

For example, the classic yellow 6″ Waterproof Boot does run a full size larger than the average shoe. Well insulated and waterproof, the Classic Yellow makes for excellent work boots because of their rubber heel, but you should purchase half a size smaller to ensure a better fit.

Although Timberland sizing will differ, many of the boots the brand offers can be worn by both men and women.

Most women’s feet tend to have longer heels and higher arches than a man’s, so subtracting two shoe sizes from a man’s shoe will lead to the correct women’s size. If a woman is a size 8, she could look for a man’s size 6. 

While this list isn’t exhaustive, here is a selection of Timberland boots to help save you time searching when trying to find a perfect fit. 

This article is a general guide to whether they run big and should be purchased in half a size smaller, run true to size, or run small and may need to be purchased in a half size larger. 

I checked out many customer reviews and used their assessment of whether or not Timberland boots run true to compile this guide. 

Men’s Holiday Lux Waterproof Boot

Size: Runs true to size

This sturdy boot, available in medium or wide, features double padded collars and Vibram rubber outsoles. It uses fewer resources to produce than other brands containing recycled material. It’s designed with its famous anti-fatigue technology and has shock absorbers.


Size: Runs a full size larger than average size

These ecologically sound shoes come in medium and wide widths for slightly wider feet. Made with environmentally sound material, they are perfect for people trying to watch their carbon footprint while still wearing leather.

Men’s Heritage 6-Inch Waterproof Warm Lined Boots

Size: Runs about half a size larger

Timberland’s Heritage boots come in wide and medium. These boots, when properly fitted, should feel a little bit tight, so opt for a slightly smaller size to have them fit perfectly after you break them in. 

The Heritage boot is specifically designed for the cold weather, making them great for winter hiking or just working outside. The padded collar provides extra comfort and support, and the anti-fatigue footpad is removable. 

Men’s Boulder Hiking Trail Boots

Size: Runs slightly larger than average size

Although this is a hiking boot, it looks like a shoe and comes in medium width. Known as one of the company’s most stylish and comfortable boots, Boulder boots run big, lightweight, and perfect for fair-weather outdoor trips. 

I use these shoes as work boots and can attest that the traction is excellent.

Men’s Snowblades Tall Winter Boots

Size: Runs true to size

This cold-weather boot comes in medium width only. If keeping your feet warm on a hike is important to you or encountering snow on your travels, these are the Timberland boots of your dreams. 

They also make incredible work boots because they contain TimberDy Waterproof membranes as well as 400 grams of the company’s patented installation to keep working feet warm and dry. 

They have rubber outsoles to keep the snow far away from your feet and are tall enough for medium-depth snow.

Men’s Greenstride Edge Waterproof Boots

Size: Runs true to size

The Greenstride Edge boots come in medium and wide widths and offer plenty of room without being tight on your toes. 

One of the biggest draws of these popular boots Timberland offers is that it is environmentally friendly using a mixture of renewable natural sugar cane and tree rubber. 

Men’s 6-Inch Waterproof Field Boots

Size: Runs true to size

This popular boot only comes in medium width, but as each boot weighs only a single pound, you can carry a spare pair if you go on an extended camping trip.  

Timberlands waterproof field boots not only keep your feet dry while you’re wearing them but also contain direct-inject polyurethane outsoles to keep the water away from them. 

Women’s Timberland Premium 6-Inch

Size: Runs slightly larger than standard size

Although Timberlands gained fame making work boots for men, they also offer a variety of boots for women. They make boots that you can use for fashion, work, or play. This premium boot is the womens’ version of Timberland’s most popular premium boot. 

They come in both wide and medium and are known for being one of the most comfortable boots on the market, even if they take a bit of time to break in. 

The reviews left by say that they last for many years and, like many leather projects, only get better with age. 

Women’s Boroughs Project Waterproof Winter Boots

Size: Runs true to size

The Boroughs Project boots come in medium width only, but they tend to secure the foot loosely.

This aesthetically pleasing winter boot is in demand in reviews on Timberland’s website with a membrane made from recycled bottles.  

A warm faux fur lining and 200 grams of PrimaLoft that they contain will keep your feet cozy.

The memory foam footbed is very easy on the feet if you need to wear them for a few hours on rough or rugged terrain.

Woman’s Garrison Trail Waterproof Hiking Boot

Size: Runs half a size larger than true size

These Timberlands come in medium width, and you’ll benefit from wearing a pair of heavy socks with them even though they look like a regular sneaker. They have the insoles of a hiking boot and have excellent traction. 

Wear these lightweight and versatile shoes to go hiking, to the bank, or for taking the dog for a walk, although I found they may not be sturdy enough to use as work boots.

Women’s Timberland Heritage 6-Inch Waterproof Boots

Size: Runs slightly larger than average size

Who says that a hiking boot available in medium width can’t be beautiful and feminine as well as practical? 

This fantastic black boot comes decorated with stylish roses and contains anti-fatigue insoles which use a spring-like system to absorb and return energy to the feet.

Women’s Mt. Maddsen Waterproof Hiking Boot

Size: Runs true to size

This classy-looking and casual Mt. Maddsen boot only come in medium width. They contain the TimberDry™ waterproof membrane that Timberland is famous for in their footwear.

The medium height makes them sturdy enough for hiking or work but is stylish enough to wear to school or around town.

Customers say that these boots feel comfortable right away without ever having to break them in. You can go for a hike a few days after you buy them, which is a scarce quality in a leather hiking boot.

Women’s Grayson Waterproof Tall Boot

Size: Runs true to size

Although advertised at medium width, some reviews say that they found this boot style narrow in the toe. Wearing them a bit might help make them more comfortable but always choose boots that aren’t too tight for you. 

These fashionable kicks measure up and protect your feet from the rain as you go about your day using 50% recycled bottles. They contain MirrorFit for your comfort and will look great with many outfits. 

Can I Return Them If the Timberlands Run Big?

If you buy one of their products online and it does not fit, Timberland boots have a free return policy. 

When you get a shipment from Timberland, they include a return shipping label. You have 60 days to make sure your boots fit. 

If you buy Timberlands from an outside retailer like Amazon, you should check their policy before purchasing.

Final Thoughts

Do Timberlands run big? Sometimes Timberland boots run big, but they run big for both men and women, and it’s often on purpose. 

These shoes have a design that provides comfort for many different activities. Measure your feet before you purchase online to help you find the right fit, and if necessary, Timberland boots have a good return policy.

They continue to try and make their products more environmentally sound, and they offer a canvas line of shoes for vegans as an alternative to leather. 

If you work, exercise, or play outdoors, you need boots that fit and keep you safe from the elements. When your shoes fit correctly, they can make your outdoor adventures safe and fun.