Why Do Timberlands Hurt My Ankles? (What To Do About?)

If you’ve ever worn a pair of Timberlands, you may have experienced this painful (and annoying) sensation: your ankle starts burning and stinging as if someone is pressing a hot iron to it. Needless to say, that’s not the feeling you should get while wearing a pair of boots. But what causes this painful situation, and how do you prevent it from happening?

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Timberland boots are some of the most comfortable boots on the market. However, like any other boots, they require a break-in period.

There is no doubt that Timberlands are built to last and are one of the most durable footwear options out there. But because of their durability and ruggedness, they tend to be tough on your ankles during the break-in period.

Why Do Timberlands Hurt My Ankles?

What causes this ankle pain? In order to understand why Timberlands hurt your ankles, you need to understand what makes them so sturdy and comfortable in general.

The secret lies in the boots’ distinctive features. Timberland shoes are waterproof and have a rubber sole that is supposed to resist wear and tear. They also have a unique heel that has an internal piece of rubber that supports your foot while providing stability when walking. This gusset holds your foot in place while also cushioning it from shock resulting from every step you take.

So the reason why timberlands hurt your ankles at first, it’s because of the part of the gusset that is right behind your ankle bone (or “navicular bone” if you want to sound smart). The part that hugs your ankle is made of leather, which takes time to loosen up, but once it does, they feel great!

A much-needed break: When you first wear your new pair of Timberland shoes, it’s normal for your feet to feel discomfort due to the tightness of the boots all-around your feet.

Why Do My Ankles Hurt Wearing Boots?

The problem of ankles hurting with boots is not unique to Timberlands with most quality boots needing a break-in period.

What Causes It?

There are two reasons that cause this phenomenon: friction and pressure. The rubbing of your skin against the inner lining of your boot causes friction, which then results in that uncomfortable feeling. Because the ankle is not as thick as other parts of your body, the rubbing tends to be more intense there.

The pressure on your ankles also comes from above: when your foot moves around inside your boots, it pushes down on your ankles so that they move inwards towards the center of the shoe. This makes the lining rub against them more intensely.

Other factors, however, could be…

  • Wearing boots for extended periods of time especially if standing and walking or running around can cause strain on your ankles.
  • Ankle pain can also easily result from boots that are too heavy such as work boots especially those with steel toes.
  • Boots that are too big or too small can also be a culprit of ankle pain.

When choosing boots be sure to select ones that fit properly to your foot not only in length but also in width. If you need steel-toed boots for work, try a lighter-weight alternative such as composite toed boots.

How Do I Stop My Timberlands from Rubbing My Ankles?

There will be a period of breaking in your Timberlands where they rub your ankles. Wear thick socks or bandaids to protect your ankles during this time.

Most boots, Timberlands included, rub your ankles when you are breaking them in. Breaking in boots is when you loosen the leather behind the ankle after you buy them.

This is inevitable. The only way past it is through it. To avoid discomfort as much as possible, wear thick socks or bandaids on your ankles for maximum protection while you are breaking in your Timberlands. Soon they won’t rub your ankles.

However, if you find rubbing, there is a great tip for alleviating the pain until the boots are worn in.

  1. First of all, make sure that your laces are not too tight. To fix this problem, skip a hole with the laces.
  2. If skipping a hole doesn’t help, then lace the boots differently. Lace them up as tight as possible and then, after making sure they are really tight, leave the top two or three laces untied, creating a gap between the top of the boot and your calf to relieve pressure from your ankle area.
  3. Lace them like this for about a week or so and then re-tighten them as normal. The leather will soften and after a while, it won’t hurt anymore.

How Do I Stop My Ankle from Chafing?

Ankle chafing can be an extremely painful problem, but it’s usually caused by something as simple as wearing the wrong kind of socks.

Preventing an ankle from chafing is best done by wearing thicker socks that allow the skin to breathe. If sock thickness isn’t enough, then adding an extra layer of fabric to the skin will help prevent chafing and abrasion. Wearing a sock liner will help protect the skin from contact with the sock, which can reduce chafing and blisters.

There are a few different ways to stop ankle chafing in shoes, such as:

  • Wear longer socks, or double up on socks.
  • Use adhesive bandages on the back of your ankles.
  • Wear insoles in your shoes. Insoles will change where the back of the shoe touches your ankle and can help prevent chafing.
  • Add moleskin to the back portion of the shoe that is irritating your ankle.
  • Use duct tape on the back of the shoe where it touches your ankle to create a smooth surface.

The key to preventing ankle chafing is to wear socks that fit properly. Cotton socks tend to be too loose, which allows them to slide around and bunch up against your skin, while athletic socks tend to be too tight, which can cut off circulation and cause discomfort.

Does Wearing Boots Weaken Your Ankles?

Boots are among the most common footwear through winter due to their warmth and support. However, it’s this support that could potentially weaken your ankles. While wearing boots occasionally is unlikely to weaken your ankles, long-term use could pose a greater risk.

For those who have to wear boots day in day out, maybe as part of their work uniform, the muscles, ligaments, and tendons in the ankle will likely weaken over time. Anything that forces your foot and ankle into a fixed position while you’re standing or walking can create joint problems.

If you lay in bed for a prolonged period, your legs would begin to weaken as you are not working the muscle. It’s the same with your ankle; if you constantly support it, you don’t get the ankle to do any work by itself, causing it to weaken.

Overall however it should only be an issue if you never wear any other type of footwear. I certainly wouldn’t panic about wearing boots all day every day at work for example. As long as when you come home your switch out of them.


In summary, whether you’re looking for fashion or functionality in your boots, there are plenty of boots produced by Timberland that can give you that. However, the right pair of Timberlands will be comfortable and not cause pain to the ankles even when worn all day long.

When the boot is laced to a reasonable degree and fitted properly it shouldn’t hurt at all. Again if you have them too tight, yes they will hurt. On the other hand, if you have them too loose they won’t provide the support they were designed for.

So lace them up a little bit looser and then wear them in. After an hour or two, you won’t even know you are wearing work boots.

You may also be interested in… Can You Use Timberlands for Work? (Are They Good Work Boots?) and Do Timberlands Fit Big or Small? (True To Size or Not?)