12 Tricks for Breaking In Tough Boots

Break-in pain is the ultimate paradox of new boots. One day they’ll fit like a dream, but for now the elements you love, like the stiff, high-quality leather and the thickness of the sole, can make you dread wearing them. But never fear — we’ve compiled the ultimate collection of tips and tricks to make breaking in tough boots as painless as possible. Here’s how.

Dayton Service Boot single

The Dayton Service Boot is one of my favorites of all time — but that break in…

1. Start With the Right Size

Forget what you’ve heard about the leather stretching — there’s nothing you can do about a pair of boots that’s too small, back-to-front. If your toes are cramped or the width of your foot hangs over the footbed, no amount of breaking in is going to fix it. On the other hand, too-big boots will never be more than blister machines. Blisters are formed where there’s friction, and if you’re sliding around with every step, you’ll never get past the break-in stage.

If you’re not sure exactly what size you are, go to your local shoe store and get measured on a Brannock device. It’s a helpful starting point, though not all manufacturers are true-to-size. If possible, try on boots in person before you buy them, and experiment with a half size larger and smaller than your actual size. If you have to buy online, be sure to read our reviews and consider ordering a couple of sizes and returning one of them when you’re confident. A lot of boot brands are designed to fit best when you go a half size down, but not all! Luckily, our reviews have you covered.

[Learn more: The Ultimate Guide to How Boots Should Fit]

Allen Edmonds Higgins Mill steps

The Allen Edmonds Higgins Mill

2. Wear Thick Socks — Inside

Start with the thickest sock you have (or two if you can manage it!) and wear your new boots around the house. This will help you figure out if they’re the right size without getting them dirty so you can still return them. It’ll also begin stretching the leather.

Out-of-the-box leather is as stiff as it will ever be, and softens and stretches best with a combination of gentle pressure, heat, and moisture. That’s why boots are easier to break in during summer months — the combination of warmer outside temps and increased moisture from your sweaty feet (gross but real) is the ideal set of conditions for loosening the leather fibers. The bulky socks will mimic some of this by warming up your feet and pressing on the upper, helping it mold to the shape of your foot.

3. Slap on a Band-Aid

Once you’ve worn your new boots for a bit, it’ll be pretty clear where blisters will form on your foot. You don’t have to be a martyr to them – just note those places and slap on a band-aid the first few times you wear your new boots out in the world. A little bit of preventative medicine goes a long way here. Large, fabric band-aids work best for this, as the plastic ones tend to get slippery and don’t stay in place as well.

Red Wing moc toe front askew

My first pair of boots, the Red Wing Moc Toe. Break in was not fun.

4. Bring Your Old Boots With You

Don’t commit to a 12-hour day in your new boots. No matter how comfortable they may be in your house, your arches will need a break after a few hours. It’s best to wear new boots early in the day, when your feet are fresh (your feet expand throughout the day as the weight of your body presses on them), and take them off after 2 or 3 hours. Leave your old boots by your desk or in the trunk of your car and swap them out when you start to feel discomfort.

5. Give It a Break

As tempting as it may be, don’t wear your new boots many days in a row. The moisture from your foot takes more than a night to evaporate fully, and giving the leather a day or two in between wears will not only give your feet a much-needed break, it will give the boots time to dry fully before you wear them again. As an added bonus, using this method throughout the lifetime of your boots will keep the foot-stink to a minimum. We recommend using shoe trees between wears to help draw out the moisture and so the boots retain their shape.

[Learn more: 3 Reasons Your Boots Need Shoe Trees.]

thursday vanguards river

The Thursday Vanguard boot.

6. Work the Bend

There are two main places where a boot bends: at the ankle, and just below the toes, at the ball of the foot. Those are the places that the leather will flex as you take a step, and need some work during the initial break-in. When you’ve worn your new boots for a while, just after you take them off, hold the boot in your hands and work the leather, bending the sole back and forth at the crease and crushing the leather fibers around the heel and ankle. Don’t worry about being too gentle with them either. You’re not going to ruin your boots, you’re just speeding up the process that would naturally happen as you walk around in them.

7. Scuff Up the Heels

Heel slippage is a super common problem (especially with boots that have a smooth leather lining) and as we know, friction causes blisters. Over time, wearing the boots creates a “heel pocket” in the inner heel area, which is why boots don’t give you blisters forever. You can speed the development of the heel pocket by taking a piece of fine-grain sandpaper and lightly sanding the inside of the heel area. You might be cringing at the thought of damaging the leather, but you don’t need to go crazy with it – just scuff it a bit so that the boot can grip your sock a little better and reduce the friction.

leather conditioners

8. Treat Your Leather

This method is most useful if the leather upper feels too tight: adding moisture in the form of a leather softener, like Tenderly Leather Softener, or a conditioner like Venetian Shoe Cream, can increase the give of the fibers. Remember: moisture helps leather stretch. Just be careful not to over-condition, which can make the material floppy. A little conditioner goes a long way.

9. Stretch It Out

If you’ve got a lot of tightness in the width of the boot (and you’re sure it fits right everywhere else) then a shoe stretcher is the way to go. It looks a bit like a cedar shoe tree, except with a crank that you can use to increase the width of the wooden foot. Best used in combination with a conditioner or leather softener, you just insert it into the boot, crank it open, and leave it there for 6-8 hours.

Oak Street boots laces

The Oak Street Trench Boot

10. Try A Different Lacing Combo

If you’re encountering tightness around your arch or ankles and want to give your foot a little more room to flex, skip some of the eyelets when you lace up your boots. After all, the point of the break in is to stretch the leather, not the laces. This can be particularly helpful when you’ve got a pair of boots with a gusseted tongue, which adds extra bulk to break in.

11. Take it to a Professional

If you really can’t stand the idea of breaking in your own boots, then a cobbler can help. They have specialized stretching tools that can expand just the problem areas on a pair of boots, or add padding to an insole or arch. A quick Google search for “shoe repair near me” or “cobbler near me” will turn one up, just keep in mind that you might need to leave your new boots with them for a few days.

studio d'artisan jeans

12. Don’t Rush It

A final word of warning: there are a lot of terrible DIY tips on the internet for “breaking in boots fast!” Don’t buy it.

Don’t fill your boots with water and let them dry. Don’t wear wet socks around. Don’t blast your boots with a hair dryer. Don’t spray your boots with a combination of alcohol and water.

The internet is full of terrible ideas – use your common sense. Too much water can cause the leather and other materials (like cork midsoles!) to rot, warp, or shrink. Wet socks are guaranteed to give you blisters. A hair dryer will suck all the natural moisture right out of the leather fibers. Not only will alcohol eat the dyes out of your boots, it will increase the brittleness of the leather which can lead quickly to cracking and other damage.

Go slow, pay attention, and remember that breaking in quality boots is a process that takes a couple of weeks, tops – hardly a trade-off when you think about the years of comfortable wear you’ll get out of them after it’s done.

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Mel Compo

Mel Compo is a writer, editor, and general word-geek from Brooklyn, New York. When they’re not writing about the finer side of men’s footwear they can be found lurking around the streets, trains, and museums of NYC, ostensibly doing something urgent but actually just looking around for menswear style inspiration.

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