The Ultimate Guide to How Boots Should Fit

“Which way do they stretch? Are they even going to stretch? I know I’m a size 11.”

The pressure is on when you try on a new pair of shoes in the store and things can get even more confusing with boots, since you have you can’t test the toe box, you have to consider heel slip, and many guys are taught to ignore initial discomfort in case the shoes just need to be worn in.

If you’re buying them online, things can be even tougher. Nobody wants to go to the post office — sometimes more than once — to return boots only to receive a less comfortable fit ten days later.

The Health Consequences of the Wrong Boot Size

“One of the things about wearing any shoe that’s too small is that it can compress the front of the foot and you can wind up with structural problems like bunions and hammer toes,” says Dr. Neal Blitz, DPM, FACFAS, a foot surgeon based in New York and Los Angeles who is board certified in both foot surgery and reconstructive rearfoot and ankle surgery. “If you wear a shoe that’s too big, your foot won’t bend at the shoe’s break point where it’s meant to and the arch support can be in the wrong place. That can cause inflammation, flat feet, and plantar fasciitus.”

While Blitz has made a comfortable living from bunion surgery, no one wants you to suffer in uncomfortable boots. These are are the five most important things to keep in mind when trying on a pair of boots.

thursday vanguards river

The Thursday Vanguard boot.

The Flex Point

This is arguably the most important component of fit — not the width, not the heel, but where the boot breaks on your foot. No need to overcomplicate this one: every boot has a natural break point where it wants to bend, be it at the end of a stitched toe box or simply where your toes start, but that’s what you need to remember. The boot must flex where your foot does, and that’s at the toe line.

It may sound simple but if a boot breaks in the wrong spot it will rub against your foot, your foot will slide back and forth when you walk, the vamp will crease and twist, and the toe box can pinch down on the toes.

You might be able to check the flex point by checking the shoe width. The widest part of the shoe should line up with the widest part of your foot, meaning the ball.

Alden Indy 403 sole

The sole of the Alden Indy 403.

The Heel

The next most critical part of the fit is the heel, and it might be the most controversial. Is it OK to have some heel slip?

A lot of brands won’t slip if you’re wearing the right size but if everything else is fine, a little heel slip — like a quarter to a half of an inch — is acceptable when you’re trying on well-made boots. In fact, some people find that boots with zero slip on the first wear can be too stiff on the foot, particularly if they have very stiff soles. So don’t worry if there’s a little slippage.

As the boot molds to your foot, the slip should decrease and may vanish altogether. In any case, what’s more important than slippage is that the boot moves with your foot and you don’t feel like your foot is moving around the inside of the shoe.

If the slippage doesn’t fix itself in a few months and it’s bothering you, there are plenty of cheap products, like Heel Snugs, that can easily remedy the issue.

Red Wing Iron Ranger fit

The classic Red Wing Iron Ranger.

The Width

This is where people get sloppy. A lot of guys say that if the width is uncomfortably tight, it’ll eventually stretch. This isn’t a great strategy.

“Some brands will be geared toward a wider foot and some toward a narrower foot, and that’s more of an issue than the length,” says Blitz. “If there’s too much compression at the ball of the foot, that can cause discomfort and inflammation.”

It’s crucial to remember that the length of your foot won’t change throughout the day, but the width will. Your foot is more swollen toward the end of the day, and that’s when you should be trying on shoes and measuring the width in a store or with a Brannock device. (Bring thick socks as well, since most boots are designed to be worn with them.)

One more important point: a lot of folks say that you should never under any circumstances by a boot with the expectation that they’ll stretch. This is a decent rule to follow, but note that most boots will stretch — but only about a millimeter.

Like the look of these? Take a look at the Allen Edmonds Higgins Mill.

The Arch

Arches are tricky. Many boots don’t have much in the way of arch support. Does it really matter?

“I think you need to know your foot. Do you have a flat foot or a high arch foot? That determines what you’ll be comfortable in,” says Blitz. “If you have a flat foot, you probably need a boot with some arch support. On the other hand, if you have a foot with a well-maintained arch, it probably doesn’t matter as much.”

He suggests a simple way to test this: step on a brown paper bag with wet feet. If the footprint left behind is flat from heel to toes, you’ve got flat feet. If there’s an arch and the inner sole doesn’t leave a mark, you’ve got yourself a good arch. It’s not the end of the world If your feet are flat and your favorite boot doesn’t have support — there are some ultra thin orthotic soles you might be interested in.

When sizing the foot on a Brannock, many people focus more on what their arch length suggests their shoe size is rather than what is suggested by the actual length of the foot. Your arch determines the widest part of the foot and how your foot will be supported in the boot itself, so if your heel and width fit fine in more than one size, and one size fits your arch better — this is an unlikely scenario, but it happens — you might want to pick the boot with your arch size.

Red Wing Iron Ranger finish

The Toe Box

“One challenge you have with boots is that normally, you base the fit of a shoe shoe on using your thumb to see where the tip of the big toe meets the end of the boot,” says Blitz. “But with boots, the toe boxes are generally a lot stiffer so it’s harder to gauge.”

The first thing (and often the only thing) people do when trying on sneakers is to ask how much room should be in the toe of a shoe. Ironically, it’s probably the least important thing about a boot’s fit.

Never size down to reduce toe room. Everything above is infinitely more important. A small toe box can rub your feet and cause calluses, and there’s no downside to a larger one if your heel, flex point, and width are fine.The toe box might be important for style, but it’s not a huge component of fit unless it’s way too tight.

Thursday Boots President steps

Wrapping Up

These are the five most important components of landing on your size, in descending importance. Largely, it’s all about the flex point, heel, and width. Remember that sometimes, even if your heart is set on a brand, your foot just won’t fit. This is a particularly important point for our wide-footed brethren. That a brand just isn’t for you can be a tough pill to swallow, but remember to do right by your feet. Don’t wear boots that take from you.

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By day: Manhattan-based journalist with reporting experience on four continents, published in Vice, Men's Health, Popular Science, and a bunch of other places.By night: ravenous consumer of anything and everything related to high end men's boots.Stridewise is where I nurture a maniacal obsession with footwear and share my findings. Say hey: [email protected]

24 thoughts on “The Ultimate Guide to How Boots Should Fit”

  1. Can you jsut make a basic page with your sizes in each pair you review? Would make it super easy for the rest of us to figure out which size would work for us for which boot without having to try on new brands in a bunch of sizes to find our fit.

  2. This was a very informative write-up! I have short, wide feet, so I’ve always been worried about the amount of space in the toe box of my boots, but this cleared things up for me.

  3. You got me when you said that you can end up having bunions and hammer toes if your feet are going to be too compressed because of too small shoes. My plan is to buy boots for my husband. I want him to be comfortable when he wears the boots that I will buy for him so he can use on a daily basis. Maybe, it’s best for me to accurately get his feet’s size. Thanks!

  4. Great stuff! I was kinds worrying about the fit of my purchase, (a bit loose in the front) but now I’m all reassured. Also, great look on those steps in the picture, very nice boots. Regards from the Netherlands.

  5. You got me when you said that it’s crucial for you to measure the width of your feet to make sure that you won’t end up having swollen feet. I will share this with my friend who’s interested in buying military shoes. His feet are wide, and he got them from his dad. He said that he doesn’t want to feel uncomfortable while wearing his military boots because he expects them to be used a lot.

  6. I like to echo the earlier poster’s idea of a chart of your sizes. For example, I am a 12.5C on the Brannock device, meaning I can wear anything from an 11 to a 13 in most shoes/boots. You’ve mentioned in a few videos that you are usually an 11, so it would be helpful for people to guess less about fit in specific brands to have a reference point. Of course, this is complicated somewhat as many brands have multiple lasts, but Red Wing has most of theirs on two lasts (8 and 23) while Allen Edmonds has literally dozens and correct size in that brand can vary a full size. Thanks again for a great YouTube channel and for providing a helpful service to prospective buyers.

  7. Knowing how boots should fit will hopefully mean the next time you invest in some new boots, they will feel like a second skin. You won t know you have them on your feet, even when you have been wearing them all day.

  8. I’ve got about an inch in the toe box of my Thursday’s and Iron Rangers. The heel and everything else fits snug. I’m a 9.5 in Thursday and IR, and 10.5 everywhere else. Is that room in the toe box okay?

    • Hey Matt, that’s quite a lot of room in the toebox but if the heel is snug and the toe break is fine, I don’t think it’s a bigggg deal. Just make sure your toes are breaking in the right spot.

  9. Thank you for this. As I’m getting into nicer boots, this is very helpful. What’s your opinion here? As a comparison, I wear an 8.5 in the Thursday Captain, which fits really well. Because they were clearance, I had the opportunity to get some decent Allen Edmonds boots for a good price, the Dalton and the Sullivan Street. Both are built on the same last. In the Dalton, I ordered an 8.5E and a 9E and found the 9E more comfortable and kept them. The comfort issue has to do with the instep of this last. Felt too tight on the 8.5E. The length of the 8.5 was probably optimal but the difference is minimal and the flex point is still fine. There was not a 9E available in the Sulliavan so I ordered an 8.5E and an 8.5EEE. Same issue with the 8.5E. The 8.5EEE feels much better. To be honest, it doesn’t feel that much different than the 9E Dalton. Maybe a hair more slippage in the heel but nothing at all extreme. And just a bit more snug in the instep but it seems like the width increase mitigates that to some extent. And strangely, when laced, there is no discernible difference where the laces pull together. I expected the 8.5EEE would mean a smaller gap. QC issues? Not sure. Either way, is it okay to wear two different sizes in the same last? I feel as long as both are comfortable and meet your criteria, it shouldn’t matter.

    • That was quite a tale! Yeah I think so long as it’s comfortable and the toe break is where you want it to be, it shouldn’t be an issue. Good purchases, by the way! Hope they work out, Michael.

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