Work boots are built to be rugged and safety-compliant first, with comfort coming in (a sometimes distant) second.
But come on, if you’re going to be spending all day on your feet, you deserve to be more comfortable. Otherwise, those long hours at work are going to feel even longer and leave you exhausted.
Luckily, in just a few simple, largely inexpensive steps, you can make your work boots more comfortable in no time.
What You’ll Need to Make Work Boots More Comfortable
- Measuring tape or ruler
- Boot care kit (with leather conditioner like Venetian)
- Insoles, marker, and cutting blade or scissors
- Moleskin padding and scissors
- Boot stretcher
- A good pair of work socks
8 Ways To Improve the Comfort of Your Work Boots
1. Ensure You Have the Right Fit
When most of us think about the “right fit,” our minds instantly go to shoe size. The length of our feet is the most common metric to measure—not to mention the easiest one.
To make sure you’ve got the right size for your feet, whip out your nearest tape measure or ruler. Place the measuring tool of your choice on the floor, and place your bare foot on it. Take the measure from the tip of your heel to the tip of your big toe. The nearest size up from that measurement is the right fit for you.
Now, be aware that feet are often different sizes. Always size according to your largest foot.
But length isn’t the only measurement that matters. You also need to think about width. In fact, it may be even more important than length to the comfort of your boot.
You see, your feet may actually grow wider as you age. As the tissue in your feet loses elasticity (a common downside to aging), your arches may sag, and your feet grow wider.
This means the boot width that fit you when you were younger may no longer suit you. And let me tell you, as a guy with wide feet, boots that are too narrow are almost more uncomfortable than boots that are too short.
Pay attention to how the boots feel, not only on the tips of your toes and heels but also on the outsides of your big toe and little toe.
If your toes feel squished against the sides of the boots, it may be time to get a size wider:
- D becomes E
- E becomes EE
- EE becomes EEE
2. Break Your Work Boots in Properly
Take it from a guy who’s broken in many pairs of leather boots and shoes: if they’re not properly broken in, they’re going to be very uncomfortable.
The leather used for work boots tends to be highly stiff initially and needs time to soften before it molds to the shape of your feet. But waiting for that to happen naturally could lead to a few weeks of serious discomfort.
It’s better to be smart and speed up the break-in process.
We’ve got a full article on how to break in work boots that you can read for longer, more detailed instructions. The basics, however, are fairly straightforward:
Step 1: Wear thick socks (see the “Invest in Work Socks” section below) to protect your feet and expand the boots from within.
Step 2: Walk around your house for 15-20 minutes at a time, or an hour or two each day. Once the boots begin to soften and feel more comfortable, start wearing them around your house all day long. Walk up and down stairs, and actively soften the boots by placing them on a step and rocking your foot back and forth.
Step 3: Take the boots for a walk outside. Start off with a short walk—15-20 minutes at first—and start wearing them for longer and longer as they conform to your feet.
Step 4: Use your hands to bend the midsole of the boot. Step on the heels to relax the really stiff parts.
Doing this daily, you’ll need about a week (max two) to break in the boots but trust me, it’s worth the effort. They’ll be incredibly comfortable once properly broken in.
3. Condition Your Boots for Better Comfort
Applying leather conditioner, mink oil, or moisturizer does wonders to relax the stiff, tight fibers in the leather. It’s a highly efficient way to speed up the softening process and break the work boots in faster.
Ideally, you should consider buying a boot care kit from the brand that crafts your work boots. They typically know how best to treat the leather, and you’re less likely to damage higher-end work boots than if you use a generic “one treatment serves all” kit.
Take the time to apply the conditioner, oil, or moisturizer, using a cloth to rub it gently into the leather. Once the conditioner is fully dried, slide on the boots and go for a walk in them (around the house or outdoors).
You’ll be surprised at the night and day difference it’ll make—and it’ll speed up the breaking-in process.
Bonus: If you get in the habit of conditioning and treating your boots right out of the box to soften them, it’ll be easy to sustain that habit. Boots need treatment every three to six months to keep them in great shape.
After testing 10 of the most popular leather conditioners, Venetian came out as my top pick because it nourishes leather, doesn't change the color, and actually adds a decent amount of weather resistance as well.
4. Add Boot Insoles
It is amazing how much of a difference a good pair of insoles can make.
Most work boots come with some measure of cushioning and support, typically in the form of a foam or polyurethane footbed.
However, that cushioning may not be quite enough (especially if you’re a big, heavy guy like me), or it might compress or wear out within a few months of long work days on your feet.
Work boot insoles let you add extra cushioning and impact absorption back into your boots, even if the integrated footbed or insole is insufficient or worn out.
With boot insoles, you have the option to customize the arch support based on your arch height, be it high, normal, or flat. You can also find insoles that offer thicker cushioning to reduce fatigue, as well as odor-killing insoles to keep your boots from stinking after long, sweaty days.
Once you’ve got the insoles, it’s usually fairly easy to fit them into your boots.
Simply slide out the removable factory insoles, place them atop the new insoles, and make sure the heel and forefoot of both insoles are aligned.
Use a marker to trace the outline of the factory insole onto the new insole, then use a cutting blade or pair of scissors to cut the new insoles to the right shape. Slide them into your boots, and you’re good to go!
The Ramble is my favorite insole that I've tried from Tread Labs. It offers plenty of cushion for the ball of my foot, and the extra flex in the mid-foot boosts the stability of my boot without affecting my arch too much.
5. Apply Moleskin to Problem Areas
Moleskin is an amazingly practical pain-preventing solution for work boots—and every pair of shoes you own, really.
It’s made from a cotton flannel that acts as a layer of cushioning to reduce friction between your skin and the material of your shoes. Thanks to its adhesive backing, it can stick to both your feet and the walls of your shoes, depending on which you prefer.
Runners typically adhere the moleskin to their feet. For work boots, however, it’s better to stick the moleskin patches onto the boots—that way, it will keep protecting you every day until the moleskin wears out and needs replacing.
Once applied, slide on your work boots and take them for a walk outside. Give yourself anywhere from fifteen to thirty minutes of walking, enough time for the friction and pressure points to start making themselves felt.
Mentally mark the spots in your boots that are causing pain. When you return after your walk, use a pair of scissors to cut the moleskin patches to the correct size and shape. You don’t want the patches so large they cause friction on other spots on your feet, but you equally don’t want them so small they fail to offer sufficient protection everywhere it’s needed.
Once the moleskin is cut to the right size, use the adhesive backing to stick it to the inside of your shoe, making sure it’s smoothed out and secured properly
Take the boots out for another walk and see if the moleskin solved the friction, rubbing, or pressure problems. Re-trim, adjust, or re-apply the moleskin patches as needed.
Important Note: The moleskin may cause your boots to fit more tightly because it’s another layer of fabric atop the boots’ existing fabric or material. If the boots are very tight already, you might want to consider stretching them (see the next step) rather than adding moleskin patches.
6. Stretch Your Work Boots
Boots are typically constructed to fit a little bit tight on your feet. That way, they can relax and expand to fit your feet just right, rather than your feet swimming inside oversized boots right out of the box.
Rather than waiting for the slightly too tight boots to stretch out over (painful) days or weeks of wear, you can use a handy dandy device called a boot stretcher.
A boot stretcher is a wooden foot-shaped device with a turn-screw mechanism that lets you slowly expand the boot from within.
Simply insert the boot stretcher, twist the handle to expand it sufficiently to press against the boot’s interior, and lock it in place for a few hours to let the pressure expand the leather. Remove it, test it, and continue expanding as necessary. Use the inserts to expand specific pressure or pain spots.
Repeat the process until the boots are sufficiently stretched out that you no longer feel the pain. As you wear them and your feet expand, they will continue to mold to your feet until they become the ultra-comfy work boots you deserve.
FootFitter Boot Stretcher features a dense Beech Wood base with a long-jointed handle made from stainless steel, which adjusts with ease. This construction will stand the test of time and can even last longer than your boots!
7. Invest in Some Work Socks
A good pair of work socks provides excellent protection against not only friction but also sweat, odors, bacteria, and both cold and heat.
Lightweight summer work socks will be breathable, moisture-wicking, and quick-drying, so you never have to worry about swampy feet, even on hot days.
Heavy-duty winter work socks will also be breathable, moisture-wicking, and quick-drying, but will feature extra insulation to shield your feet from freezing temperatures.
Because they’re made of heavier, thicker, more work-friendly materials (typically a wool and synthetic blend), they’ll keep the boots from rubbing against your feet and causing pain or blisters.
We’ve done the research to bring you a list of the eight best work boot socks for any situation. But honestly, my go-to socks are typically the Camel City Mill Lightweights for the majority of the year, and the Camel City Mill Heavyweights when the winter chill sets in.
Made in the USA from Merino wool, these work socks really are something else in terms of quality. They feature compression through the arch and calf which helps your feet recover after a long day. Plus, because they're Merino wool, they're breathable and help reduce foot sweat.
8. Switch up Your Lacing Method
It may sound insane, but it’s true: the way you lace up your boots will directly impact your comfort.
If your laces are pulled too tight at the bottom, they may squeeze your toes. Pulled too tight in the middle, and they can apply pressure on your arch and the top of your foot. Pulled too tight at the top, they can squeeze your ankles, causing pain and even reducing circulation.
There are a few common lacing methods, but for my work boots, I’ll typically opt for the criss-cross standard lacing technique or the Italian corkscrew if I want my boots to look a bit sharper and more stylish.
Goodbye Pain, and Hello Comfort
You’ve already got a hard work day ahead, with all the usual aches and pains that are part and parcel of long hours on the job. Why add foot pain into the mix on top of all that?
In just a few simple steps, you can drastically improve the comfort of your boots and protect your feet against squeezing, crushing, pinching, and rubbing.
Be smart and take the time to treat your work boots using the methods I shared above. You’ll never regret it—on the contrary, I promise you’ll be so glad you invested the effort that you’ll want to repeat the process with every new pair of boots you buy.
How do I make my work boots less stiff?
Leather conditioner and mink oil both relax the stiff fibers in the leather, softening them and encouraging them to flex and expand to accommodate your feet.
Using these treatments in tandem with a boot stretcher will speed up the break-in process and make the boots more comfortable in record time.
Use your hands to bend and work the midsole, and step on the heels and shafts of the boots to soften up any stiffness there.
How long do work boots take to break in?
Without any of the interventions I listed above, you can expect a pair of work boots to take anywhere from 60 to 100 hours to break in.
Typically, this is spread out over the course of a few minutes a day at first, then to a few hours as they become more comfortable, until by the end of the second or third week, you can wear them for a full day at a time without pain.
However, if you use the methods I shared in this article, you can cut that break-in time down significantly.
Why do my work boots give me blisters?
Blisters are the result of excessive friction between your skin (through your socks) and the fabric or material on the inside of the boots. That friction causes irritation and, ultimately, damage to your skin. Your skin responds by creating bubbles of clear liquid (i.e., blisters) to act as a cushion against friction and to protect the irritated or damaged skin.
Is it normal for boots to be uncomfortable at first?
Absolutely! Leather is a very stiff, hard material right out of the box, and only with frequent wear will it soften to become the ultra-comfortable material it ultimately will be.