How to Break in Leather Boots and Eliminate Discomfort

Knowing how to break in leather boots is essential, and here are the best ways to do it:

  • Check the size.
  • Get a shoe stretcher.
  • Use a spoon.
  • Condition the leather.
  • Break them in slowly.

Any of the above methods will work for breaking in your leather boots—which is arguably the most unpleasant part of owning them.

Despite their essential spot in the wardrobe of every classy man, their stiffness is unmatched when new.

You can’t do anything to prevent it. All you can do is wear them and hope you don’t give up and become a fulltime sneaker-wearer due to the discomfort.

However, you can get rid of the discomfort much earlier if you know the right tricks. We’ll teach you how to do that now.

breaking in boots


How to break in leather boots

Before You Start: Check the Size

The number of people wearing the wrong shoe size is alarming. One study found that less than 20 percent of older adults wear the correct shoe size. And what comes before becoming an older adult? Being a younger one, setting the misconception of your shoe size for your future self.

Just because your foot fits in the shoe doesn’t mean the shoe fits you. So any prolonged discomfort you’re getting from leather boots may not be that they’re not broken in. They just don’t fit.

Here are a few tips on ensuring your leather boots fit:

Use Your Thumb

Ensure you can press your thumb flat in front of your longest toe. If you can, you have enough wiggle room for flexing your feet, foot swelling, and accidentally banging your toes against objects without extreme pain.

If you don’t have enough wiggle room, you’ll find your shoes become uncomfortable too quickly. And with prolonged cramped toes, the muscles may atrophy and leave you with misshapen toes. It’s especially prevalent in those with diabetes.

Having more room ahead of your thumb here is fine too, but only if you pass the other tests.

Use Your Index Finger

Check that you can slide your index finger behind your heel with no trouble. Although you want your heel snug, you don’t want chafing or restriction.

Slide your finger the whole way around your heel. If it doesn’t feel trapped or take effort, then you know your shoes fit appropriately in the heel.

Consider sliding your finger along the sides of your foot to continue the test. Although, this is easier to do in leather shoes over leather boots.

And make sure it’s not too easy to get your finger down there. Yes, it should slide in. But you shouldn’t have room to move it back and forth or have it down there without touching both shoe and foot.

Pinch an Inch

If you can pinch an inch, your shoes are far too wide. But make sure you can pinch a little boot—without hitting foot—either side of the widest part of your foot.

It doesn’t have to be much, just enough to separate the leather from your foot without difficulty. It’ll likely bend and bring the top of the boot down a little if you do this.

But, if you can’t get the leather to bend when it’s on your foot, it may be too form-fitting.

If you passed the other two tests, you don’t need to worry as much. You can stretch out the sides of the shoes with some thick socks, or the methods below. It’s part of the break-in process.

But no pinching ability paired with a struggle to get your index finger behind your heel? That’s a sign you need to size up by half or more.

Once you pass these three tests, you’re ready to learn how to break your leather boots in.

Boots on feet, and we’ll start.

How To Break in Boots: Top 4 Ways

Now that you’ve got your new boots, you’ll need to mold them to fit your feet. The break-in process stretches shoes, so allow your feet optimum comfort.

But breaking shoes and boots in can be torturous. Let’s speed up the process of breaking in your leather boots.

#1—Get a Shoe Stretcher

Maybe you’re here because you’ve already been wearing your boots all day for a week. Yet somehow, they remain painful and uncomfortable. Or perhaps the boots just pinch a little, or won’t pass the pinch test for sizing.

The boots are definitely the right size—they’re just taking forever to break in. You need outside help. You need a shoe stretcher.

At first glance, shoe stretchers resemble shoe trees quite a bit. But they have a secret: they open up, letting you stretch out your shoes.

So, figure out where your shoes still aren’t fitting. Maybe the footbed is fine, but the leather just isn’t fitting around your feet right, perhaps in the toe box, or around the wider parts of the foot.

Place the shoe stretcher into the shoe, and start twisting the handle that makes the appropriate area expand.

Start small; too wide a boot isn’t fixable. So stop turning the handle at the first creak you hear, then leave the boots to reshape for a day or two, the longer, the better.

We recommend you moisturize your boots during the stretching process to help prevent wrinkles.

After a day or more, try on the boots. If they still don’t fit like they should, repeat the process until they do.

But what if you haven’t already tried breaking them in, and want to avoid the long and uncomfortable process? That’s what our next three tricks are for.

#2—Use a Spoon

Using a spoon to break in a pair of boots sounds ridiculous. But it’s an excellent way you can quickly break in the footbed new boots.

There are two ways to utilize a spoon for the break-in process with your boots.

  1. Use it instead of a shoe stretcher on areas that refuse to stretch.
  2. Create an indent of your foot in the insole.

Nobody likes walking around in hard shoes, do they? You want your shoe to cradle your heel and the ball of your foot while supporting your arch.

And tomorrow, you want to wear these new boots for a formal event. You’ll need to circulate, walk for hours, on an already hard floor. You need some cushioning and support.

Draw an outline of your feet, cut them out, then put them in your shoes. And grab a large spoon.

Now you can gently press down with the spoon, over your heel and ball of your foot area in the cutout. Start making a little dip for them to sit into.

Don’t go too hard or too deep; you don’t want to make the shoes feel old and unsupportive. You should just create enough of a dip to give your feet a head start breaking them in.

Now that you have the shape of your foot in the shoes, too, you can see what areas might pinch. Use the spoon to stretch the sides that may pinch your foot to give those a head start.

This won’t be perfect or complete the job, but it’ll certainly help break in your leather boots faster.

#3—Condition the Leather

Before you start trying to break in your boots, condition them. It may seem pointless since they’re brand new, but it’ll soften the leather.

Softer leather will be easier to break in than hard, stiff leather. So consider using mink oil or a branded leather conditioner.

For some extra help, you can check out our article on the best oil for leather boots.

#4—Break Them In Slowly

If none of these methods are for you and you prefer to go natural, that’s fine. You don’t have to suffer through several days of pain to do it.

First, you can speed up the process by wearing thick socks. Then, go slow.

Start by wearing the new boots when you’re sitting at your desk, or even just watching TV. Wear them for a few minutes, then take them off. Later, a few more minutes. Try and get to the point where you can wear them for the duration of your favorite TV show.

Once you’ve mastered the leisurely wear, take to the kitchen and cook in the boots. Next, tackle a walk around the entire house in the boots—you may be able to switch to regular socks here, but thick socks make it faster.

This process may take days or weeks, but gradually increase how long you wear them—go from an hour-long event to an evening to an eight-hour workday.

Remove the thick socks towards the end of the gradual break-in period, and now, your new boots should be ready for comfortable use.

Once you’ve got the technique down, you can use it for every new pair of boots you get from now on.

Frequently Asked Questions

How To Break Boots In?

Break in your boots through continuous or gradual wear. You can also use a shoe stretcher or spoons to help the process go faster.

How To Break in Cowboy Boots?

Cowboy boots are often made of stiff leather, so wear them with thick socks for a few weeks, and they should break in nicely.

How To Soften Boot Leather?

Condition your boot leather with mink oil or leather conditioner frequently to keep it soft and supple. Not only will this make it more comfortable, but it’ll help prevent cracks in the future.

sw 11


Walk Away in Comfort

Now you know how to get your leather boots broken in, soft and supple, you can go forth in style and comfort.

Breaking in leather boots can be a pain, but it’s well worth the hardship. Consider the methods above and see which works best for you.

And don’t forget you can share this with all of your leather boot loving friends.


Read The Reviews First

Sign up to get our latest articles straight to your inbox.