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5 Ways to Make Your Work Boots More Comfortable (+ Fit Guide!)

December 27, 2022

5 Ways to Make Your Work Boots More Comfortable (+ Fit Guide!)

Whether you wear work boots by necessity or for style, you know that a long day of wearing them can result in some serious foot pain. The reason? Work boots are created to protect you. They include all kinds of features - from steel toes to slip-resistant materials - to ensure that you can get your work done, no matter what your job may be.

Here’s the good news: there are a variety of measures you can take to make your work boots more comfortable. Regardless of whether you’re shopping by brands, like Caterpillar, or by features, like composite toe boots, there’s a way to make these boots more wearable. Here’s how.

Getting the Proper Work Boot FitWork Boot Fit Image

One of the simplest reasons your work boots may feel uncomfortable is simply because you have the wrong size. Since work boots are built differently than regular shoes, it can be hard to tell how they should fit. By understanding the fit you’re looking for, you can avoid this issue.

Ideally, work boots should:

  • Fit tightly enough that your heel does not slip around (your heel should not move more than a quarter of an inch).
  • Have enough room for your foot to swell, as your foot changes size slightly throughout the day as you work.
  • Feel like the arch of the shoe lines up with your natural arch.
  • Have room in the toe box for your toes to move around without any discomfort, like pressure or pinching.
  • Feel snug along the top and sides of your foot so that your foot doesn't slide into the steel toe when walking.

Finally, it’s important to note that pinching and hot spots are unlikely to go away over time. If you notice these effects when trying on work boots, you likely don’t have the right size or fit.

What Features Affect Comfortability?Work Boot Comfortability Image

Work boots are designed with durability and protection in mind, which means that many of their features can also impact how comfortable the boots are. It’s important to understand how these elements interact with your feet, as well as how they can change over time as you break in the shoes.


Most work boots are made of leather, which may feel uncomfortable and tight at first. After some consistent wear, however, leather can soften and mold to your foot, making for a customized, comfortable fit.

Slip-Resistance Boots

If you get a pair of slip-resistance boots, you may find that the rubber of the sole, the tread pattern, and the sole compound feel bulky. For most people, this is simply a feature that takes some getting used to. These features ensure that you can move across treacherous surfaces without slipping or falling.


Most work boots use high-tech insulation that you’ll hardly notice. Still, if you’re coming from wearing sneakers only, you’ll likely feel like work boots are a bit clunky. Insulation, however, is critical if you’re working in cold temperatures outside.

Waterproof Boots

Waterproof boots typically have a treatment on the leather that prevents moisture from entering the boot. They also have sealed seams, ensuring that you never get wet feet. This should generally be undetectable, though the sealed seams may feel a bit restrictive. This is a small price to pay for the comfort of having dry feet.

Steel Toes

Steel toes are unavoidably heavy. That can make them feel clunky, especially if you’ve never worn them before. Don’t worry, you do get used to the sensation. Keep in mind, if your boots don’t fit properly, steel toes can add unnecessary pressure to your toes and even cause rubbing or pinching. This is a sign of poorly fitting boots - not poorly designed boots.

5 Ways to Make Work Boots More Comfortable Women's Excavator Superlite Waterproof Carbon Composite Toe Work Boot

1. Try On First

Be sure to get the best fit from the start by trying on your work boots. Wear the same socks you’d wear at work with the boots. Check that:

  • The laces secure the boot in place.
  • You have about a quarter of an inch of space in the length of the foot if you’re trying on early in the day (before your foot has gotten bigger via swelling).
  • You have some flexibility at the ball of the foot - not the arch.

2. Socks

There are socks made specifically for steel-toe boots that have additional cushioning in the toes. Consider buying some of these socks if you find that you get a lot of pain at the front of your foot or blisters on your toes.

3. Inserts

Unless you have custom work boots, you’ll likely need an insert to ensure that you get the best fit. Insoles will depend on your needs - some offer support for flat feet, others add firmness, and some add more flexibility.

4. Break Them In

As you break your boots in, they soften and begin to conform to your feet. This can be a painful process, but there are ways to expedite it. A few methods to consider:

  • Coldwater method: Place a Ziploc bag full of water in each booth, then put the boots in the freezer overnight. When the water freezes and expands, it will stretch out the boots.
  • Hot water method: Place waterproof boots in lukewarm water for about 30 minutes. Then, shake to remove excess water and wear the wet boots for an hour. Leave to dry.
  • Oil method: Apply leather conditioner or mink oil to your work boots or leather work sneakers generously, especially the uncomfortable areas. Leave the oil on overnight to soften the leather.

5. Maintain Them

If you don’t take proper care of your work boots, the leather can crack and pinch your feet. Prevent this issue by caring for your boots. Proper care will vary a bit, depending on if you have puncture resistance boots, electric hazard safety boots, steel toe boots, composite toe sneakers, or a different variety of work boots. It’s generally best to clean your boots once a month and then use a leather conditioner to keep them moisturized and flexible.

Highest-Rated Work Boots for Comfort

The best work boot will depend on your purposes. Some jobs require electric hazard safety boots, others just require steel-toe boots. With that said, there are some work boots that have a reputation for being the most comfortable overall.

Most Comfortable Men’s Work Boot: Caterpillar Second ShiftMen’s Work Boot: Caterpillar Second Shift

For men, Caterpillar Second Shift Work Boots are consistently rated as highly comfortable, thanks to their padded cuff and mesh lining. They’re even comfortable enough to wear right out of the box if you need a quick fix.

Most Comfortable Women’s Work Boots: Caterpillar Excavator Superlite

Most Comfortable Women’s Work Boots: Caterpillar Excavator Superlite

In the world of women’s boots, the Excavator is known for being highly comfortable. They’re waterproof boots, but they don’t look or feel too different from a regular pair of shoes. Plus, they feature a carbon composite toe, making them lightweight and easy to wear all day.

Ultimately, the most comfortable work boot is the one that fits properly, has been broken in, and gets consistent maintenance.

Find your perfect pair of work boots at Franky Fashion. Shop men’s work boots and women’s work boots now.


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