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How Should Boots Fit? Your Guide to Perfect Fitting Boots

William Barton

Boots, Leather, Heritage Fashion, Denim, Workwear

William founded BootSpy in 2020 with a simple mission: test and review popular men’s boots and give a real, honest opinion. Since then, we've welcomed over 5 million readers on our boot reviews and boot care guides. Reach out to him for your own personalized boot recommendation at william@bootspy.com. Or join 50,000+ subscribers on the BootSpy YouTube channel, or send him a message on the BootSpy Instagram. Read full bio.

Last Updated: Mar 15, 2024
10 min read
Key Takeaways

Your heel should have a maximum of a half-inch of wiggle room, and it should never rub in the back. The sides of your foot shouldn’t feel squeezed. Leave an inch of room for your toes, as this allows room for your feet to expand and swell throughout the day without slipping around in the boot.

When you’re trying boots on in-store, the leather toe-cap usually prevents you from really testing how much room you have for your toes. And if you’re buying boots online, it can take so much effort to return a wrong size. Will you even get the right size when you reorder?

Finding the right size boot shouldn’t be trial-and-error, and you shouldn’t have to take a guess on a brand-by-brand basis. 

We’ll break down exactly how boots should fit so you can step comfortably and confidently into your day. 

Health Consequences Of Getting the Wrong Boot Size

Getting the wrong boot size isn’t just annoying and uncomfortable. It can lead to some serious health issues if you miss the mark on sizing. 

So if you picked up a half-size too small or big and you’re on the fence about whether to spend the effort to go back to the store and exchange them, take a moment to read this for guidance.. 

Are Your Boots Too Big?

Here’s 3 things you can do to help if your boots are too big.

If your feet are sliding around in your boots, they’re too big. Michael Ratcliff, a foot-doctor in the UK, says this can cause painful short term health issues that can balloon into much larger issues if not taken care of. 

For one, a large boot can cause corns, which are pads of hardened, dead skin that form from consistent rubbing and pressure. Corns can attach themselves to deeper, softer tissue, which makes them difficult to completely remove. And for that same reason, they can become painful, too. 

If your feet slide around while you walk, chances are you’re repeatedly rubbing one discreet area of your skin. That will cause a corn, and if you aren’t vigilant, it can become a permanent fixture. 

Large boots can also cause Achilles tendonitis and damage ankle ligaments—both of which are more serious long-term health issues and may require medical intervention. 

If there’s more than an inch of room for your toes, or if your heel is slipping more than a half-inch in the back, your boots are likely too large. 

Are Your Boots Too Small?

You’ll need a boot stretcher if your boots are too small. Here’s how to use one.

Now, just because you’ve read all about the havoc big boots can cause, don’t go buying the tightest pair of boots that’ll fit onto your foot. That may create problems just as uncomfortable as corns and tendonitis.

Ratcliff says that tight-fitting footwear is a major cause of ingrown toenails, which are painful and unsightly. If your toes are jammed up, you’re likely lifting your toenails from their bed, which can allow microorganisms to enter, where they may create bacterial swelling problems. 

Boots that squeeze your foot don’t allow for much air-circulation either, which can lead to athlete’s foot—another uncomfortable and hard-to-cure problems that’s best avoided altogether. 

If you get that pins-and-needles feeling in your feet after wearing your boots for a few hours, they’re too tight. If your toes hit the end of the toe-box, you need to size up. 

7 Key Considerations For Finding Boots That Fit You Perfectly

1. Flex Point

The most important consideration to make when buying a pair of boots (or deciding whether to keep the new ones you just got) is the flex point. Take a short walk around with your boots on and note where the shoe naturally bends: this is the flex point. 

This natural crease should line up with where your foot also flexes—where your toes and the ball of your foot meet. 

Diagram of foot to show how boots should fit

If you’re wearing boots that flex in the center, or too near the toe cap (something cheap and improperly tested boots do), it can cause many of the health issues we mentioned above. The extra rubbing and lack of proper support will definitely get your puppies barking and may even lead to plantar fasciitis. 

Now, many boots are made with stiff leather and don’t flex very much. You can still see where the boot flexes, and even though it may take some break-in time (which can be painful), you’ll end up with a great-fitting pair of boots. 

Another way to check the flex point is to note the widest part of the boot. Where your foot gets wider (the ball), the boot should widen, too. 

2. The Heel

A quick video on how to tell if you have too much heel slip.

In most cases (if you’re buying a quality pair of boots), you’ll start with a little heel slippage. That’s perfectly ok, so long as your heel is only moving a quarter to half inch. Anything more than that, size down. 

Boots have a break-in period, and during that time, the insole and leather shapes to your foot. A lot of times, you’ll find that the boots you bought with a quarter-inch of heel slip fit perfectly just a few weeks later. 

If the heel never snugs up to your foot and the slight amount of room is bothering you, a heel grip can offer nice padding and solve your issue. We recommend that you break your boots in first before putting a grip on, though. The discomfort you’re feeling may just be from the stiff leather. 

3. The Width

Here’s all the different widths of boots and how to tell how wide your feet are.

Your foot is wider than you think it is. 

Wait, what?

When you wake up, your foot is a certain width, and it’s different by the end of the day. Walking and standing cause your feet to swell up to a half-size larger

For that reason, we recommend trying your boots on in the afternoon when your feet are much closer to their largest size.

And it’s not that your feet get longer, but all that swelling makes them wider. 

Boots come in six widths, from B (extra narrow) to EEE (triple wide). While most manufacturers sell boots in the D (regular) and E (wide) range you may need to find brands that offer an even greater range of widths. 

Again, if you’re feeling pins-and-needles in your feet throughout the day, your boot likely isn’t wide enough. Perhaps you tried them on in the morning when your feet were more narrow. Well now you know to account for swelling—a perfect fit in the morning can feel like a vice in the evening. 

4. The Arch

Chiropractor and alternative medicine expert, Dr. Chloe Tillman says that most people don’t need any external arch support. That’s great news for boot lovers, because boots rarely come with built-in arch support. 

However, if you have flat feet, suffer from plantar fasciitis, or need arch support for any other reason, it’s important to factor that into your boot size. Chances are, you’ll be adding an orthotic insole and that will change how your boot fits. 

The best way of figuring out whether your boot fits with an insole is to bring one with you to the store. But, if you’re shopping online, you don’t have that luxury. 

There are some very slim orthotics available, and if your boots fit well, you shouldn’t have a problem slipping these in at the bottom. 

Don’t change your boot size if you plan on adding an orthotic. Just go with your natural size—there should be enough room in your boot to accommodate. 

5. The Toe Box Room

Imagine trying on a new pair of shoes. What’s the first thing you’d check to see if you have the right fit?

You’re probably imagining yourself pressing down on the toe-box with your thumb. 

Turns out, this is one of the least effective ways to determine whether you have the correct fit. 

Sure, a great fitting pair of boots will likely leave you an inch of room for your toes, but having more space doesn’t automatically mean you should size down. 

It’s far more important to make sure your boot has an excellent fit in the width and heel. These are the areas that can really damage your feet and ankles, or otherwise make your boots unwearable. 

Having over an inch of room is fine, but anything under an inch is pushing the small side. If your toes are jammed up, you risk developing something called hammertoe. While hammertoes sound like they could be very valuable assets, in reality, they hurt tremendously. 

Getting the fit right in the toe is important, but it shouldn’t be the only consideration. If you make sure your foot is supported but not choked along the sides and the flex point matches with your foot, you’ll probably have an excellent fit in the toe anyway. 

6. Your Socks

Why thick socks aren’t always better with boots.

The socks you wear with your boots can be the deciding factor in whether you’re about to have a comfortable stroll or a medieval torture march. 

A thick pair of socks can change your effective foot size by a half-size. So that means if you wore thick wool socks to the store when you tried your boots for the first time, and now you’re wearing thin cotton socks, chances are your boots feel a little loose. 

My all-time favorite boot socks
Camel City Mill Lightweight Wool Work Sock
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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.

Check Price Read Our Review

If your feet get cold in the winter, or you want a little extra protection from the elements, it’s better to get the fit correct while wearing thick socks. True, they may fit a little loose when summer rolls around, but as your feet swell with the heat, hopefully you won’t face too many problems. 

But if you’re pushing the small-side with thin socks, you’ll struggle even getting your boots on with thicker socks. 

When in doubt, wear thick socks when judging whether your boot fits. The downsides to having a boot a half-size too big are fewer than getting a half-size too small. 

7. Arch Support If You Have Flat Feet

We covered this above, but this is specifically for the folks who know they have flat feet already. 

If you’re not sure, get your feet wet and step on a piece of paper or concrete. If your footprint shows the entirety of your foot, you have flat feet. Back when flat feet could get you out of the draft, it wasn’t such a problem. But the perks have been revoked. Flat feet need extra love through the use of special insoles and orthotics. 

My top pick for insoles
Tread Labs Ramble Insoles

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.

Buy Now at Treadlabs Read Our Review

Altering your boot fit based on orthotics really depends on the size of the orthotic. If you need major arch support, you may need to move a half-size up to accommodate a larger insole. But if you only require a little added structure, there are plenty of slim orthotics available that should fit into your boot without drastically altering your ability to wear them. 

A Cinderella Story

You’re on your feet all day. If your boots don’t fit, you’re in for some trouble. 

Sure, we’re big advocates of picking up boots that look great, but there’s no reason they shouldn’t feel great, too. 

Bookmark this article—next time you go shopping for boots, bust it out and make sure you’re getting the right fit by going down the list.

Just like Cinderella, there’s a boot out there that fits you perfectly. You just need to go out and find it. 


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  1. Paco Candano

    Question about the fit of my Caps I’m 10.5-ish on the Brannock and supposedly D wide (The device I used was not in good shape and the width part wobbled so I’m not 100% sure). Got two pairs, one 10 US from the official page with the Kingmaker last and a “seconds” 9.5 US that I think is the last before KM one (bought at less than half the price in a mexican e-commerce web called Mercado Libre that surely gets them from guys at the León factory), both in rugged and resilient leather in Arizona Adobe and Black Matte, respectively. The snugness and Thursday and everybody talks about can only be felt on the 9.5 because I can only wear them with normal socks and I have about a thumbs width of toe room, and a little bit of wiggle space, but not much especially on my right foot. I’ve walked an awful lot with them and haven’t had any issues, any discomfort whatsoever nor foot problems but I’m usure if they’re the size I should be using provided they recommend half a size down from the brannock, not a full size. On the flip side, the 10US on the KM last fit quite roomy, so much I really need to use a good quality thick (not super thick for extreme cold though) boot sock in order to fill them better and sometimes I can fit a thin insole which I take out so I can make the foot carve its form on the boots sole. Also, stupid comfortable also no foot issues, a lot more wiggle room than the others and an inch of toe space to the tip of the boot.
    I hope all of this makes sense, so what is the recommended fit then, snug 9.5 with normal socks and especially for CXL leather that will strech more than R&R or better roomy 10 US with thick ones and with fear they will stretch more with time but can be corrected with an insole? I’m unsure how to proceed when I get my third pair, which I will because these freaking boots are soooooooo good.

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