The Ultimate Guide to How Boots Should Fit (5 Areas to Look At)

“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: 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 rear foot 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 fasciitis.”

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.

[Related: My list of The Best Boots for Men]

thursday vanguards river

The Thursday Vanguard boot.

1. The Flex Point

  • Ensure your foot breaks at the widest part of the boot

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.

2. The Heel

  • A little heel slip is not a big deal and should remedy as the boot breaks in
  • Product like Heel Snugs can help persistent heel slip

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 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 will probably vanish altogether as the heel counter molds to your foot’s shape from friction and body heat. Unlined boots in particular have a nappy interior that’s extra great for catching the heel after a few wears. 

for  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.

[Related: 5 Tips to Prevent Blisters on Boots]

Red Wing Iron Ranger fit

The classic Red Wing Iron Ranger.

3. The Width

  • Buy a boot that cradles the ball of your foot — not pinches

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 buy 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.

[Related: My list of The Best Boots for Wide Feet]


wet test foot type

4. The Arch

  • Find out how much arch support your foot type needs and how much is offered by the brand

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.

[Related: The Best Insoles for Boots]


Red Wing Iron Ranger finish

5. The Toe Box

  • This is largely irrelevant if the rest of the boot fits well

“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: if the previous four sections in this article are on point for you, the length is basically irrelevant because your foot will be moving well with the boot.

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 feel right. 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.

FAQs How Boots Should Fit

How do I know if my boots fit properly?

There are five areas to check. They are: the flex point, the heel, the width, the arch, and the toe box. Your boots should not feel tight. They should feel snug on the forefoot, they should have plenty of room in the toe box, and the heel should not slip more than a quarter of an inch.

How much room should be in a boot?

There should not be too much room or movement in your boot. It should feel snug around the forefoot. You do not want it to feel too tight. You do not want your foot to slide forward. Your heel should not move more than ¼ of an inch.

Is it better for a boot to be tight or loose?

Too tight and too loose are both indicative of a bad fit. Leather boots will stretch slightly if your boot is slightly tight. If your boots are too loose you can wear thick socks, buy insoles, or both.

How tight should boots fit at first?

Your boot should feel snug around the forefoot. You should not feel any discomfort or pain.

How to tell if boots are big?

Your boots are too big if you’re foot moves forward in the boot and hit the front when walking downhill. Your boots are too big if you have a lot of extra laces after you time them. Your boots might be too big if your heel moves more than ¼ of an inch.

How much room should be in the toe of a boot?

There is a lot of leeway with how much room you can have in the toe of your boot. You are fine as long as the flex point of your foot matches the flex point of the boot and your toes do not press against the boot.

Should boots fit tight or loose?

Slightly too tight when wearing your thickest socks is fine, your boot will stretch but only a little bit. Slightly loose with your thinnest socks is ok as long as you don’t feel any hotspots when you walk.

How should boots fit around the calf?

You want your boots to fit snuggly around the calf, more importantly, you want to make sure you can easily get them on and off.

How should boots fit around the ankle?

Boots can be loose or snug around the ankle depending on how tall they are and how tightly you lace them. You do not want them to be uncomfortably tight. If they are new the leather will soften over time.

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Nick English

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]

69 thoughts on “The Ultimate Guide to How Boots Should Fit (5 Areas to Look At)”

  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.

          • I bought a pair of Red Wing Iron Rangers in size 10 D. Still breaking them in, but I feel the pinky and ring toe hitting the front of the boots now (I didn’t in the store). Would you recommend I go to a 10.5D or 10E? In running shoes I wear an 11, but most of my dress shoes are 10. Thank you!

          • Hey Sun, sorry for the delay I’ve had a crazy spam problem. Interesting that didn’t happen in the store, but it sounds like you could get a cobbler to stretch the boots. Keep breaking them in for a couple of weeks, see where they’re at, and get ’em stretched, I think you’ll be OK

    • Bear in mind, military boots are not the same as work or cowboy boots. The fit is designed for a “general” person. There is also variance between manufacturers, even with the same NSN. I love most of my military boots (still have a lot of them) but they can vary widely, even when having the same size and manufacturer.

  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.

  10. When it comes to boot sizing, I always use this article as a reference guide. Helped me find a pair of Chelsea boots with Blundstones that I’m satisfied with. Thanks!

    • Great! Ironically I got the wrong size TWICE with Blundstones, I kept mixing up the Australian/American sizing, haha. I’ll get a review done eventually though!

  11. Nick, I’ve bought two pairs of 875s. 11.5d and 12. On a brannock i am 12. The 12d need insoles and think socks to fill up room, so my feet don’t feel like bells ringing, and tons of heel slip. The 11.5d seems better. My left foot feels like the perfect amount of toe room. The right foot has the left corner of my big toe slightly rubbing against the “front curve” of the toebox. Will this go away with wear?

    • Hey Jeff! Yes you need to size down with those shoes. 11.5 is for sure the right size for you, keep wearing them and if the toe rub is stil bothering you in a month or two, ask a cobbler to stretch them a little.

  12. Hi, recently bought some iron rangers 8111 and they seem to fit okay, although I’m wondering how much they stretch, possibly becoming too large after break in. I own some boots with chromexcel leather and found they stretched quite a bit. Can I expect the same with the iron rangers? Fan of your work and found this guide really useful!

    • Hey William, Iron Rangers don’t stretch as much as Chromexcel but if they fit now, I wouldn’t worry about them stretching to be too big. They’ll mold to the shape of your foot. Glad you like the site!

  13. Hi Nick! Big fan of your YouTube channel, and your reviews. I recently bought Red Wing 875s (been looking at them for a long time and finally pulled the trigger.) I’m very worried that I bought the wrong size. I wear a 14 in sneakers and all my boots (Thursday Captains, Doc Martens, Cole Haan) are size 13. I bought the Red Wings in 13 because they felt snug but I can wiggle my toes freely…as the website suggests. My laces are about 1” apart as is also suggested by someone, and I don’t notice much heel slip…but there is a generous amount of space in front of my big toe…I just have a feeling they are too big. What do you think?

  14. For years, toe box room has been my most important criteria when sizing boots. The goal was to get my toes as close as possible of the tip of the boot but without touching, the sweet spot. But you’ve made me see how it is actually the least important of the list of fit criteria. Perhaps I intuitively believed that shoes should fit like gloves. You want your finger tips snug to the tips of the glove, right? So the tips of the toes ought to fit snug too. NOPE. Great article.

  15. Nice article bro, I worried about the fit of my purchase, but now I’m all reassured. Also, great look on those steps in the picture, very nice boots.

  16. Do you have any advice for those of us with narrow feet (AA/AAA)? Or even B? I noted the wide foot buying guide, and the tip in the Redwing vs Wolverine review (narrow is out of luck!). Best I’ve found is that Truman and Allen Edmonds offer B. Thanks!

  17. Hi Nick,
    Great article and amazing channel, thanks!
    What would be your recommendation for a roomy toe box boot.
    I love the look of the Thursday Captain but they are way too narrow at the end.
    ( My foot width is 4″ but one toe seems to rub against the end and that can drive me nuts)


    • Roomy toe box, many recommend Alden’s combination last, which is narrower at the heel than the forefoot! White’s 350 Cruiser is also nice and roomy

  18. Hi Nick, thanks for the great and useful post! I recently bought a moc toe boot size 11, which I find a bit loose even wearing thick socks. It only gets a better fit if I use insoles and thick socks at the same time. That’s what the seller recommended me. I’m usually a size 10, but when I tried this size in the shop, wearing thick socks, while I felt it had the perfect snug around the heel and the sides, when I walked I could feel my toes (mostly the second toe) touching the tip of the boot . I have a greek foot, so my second toe is the longest. My left foot which is a bit longer than my right one measures 28cm. I tried to measure the fixed insole in the size 11 boot and i think it measures 29cm. Do you think I should go back in the shop and get size 10 and eventually the boot will stretch and my toes won’t touch the tip? Or do you think a cobbler can stretch the boot to make a bit more room in the toe area? I feel like perhaps a size 10.5 would have been the right one but the shoe maker doesn’t make half sizes unfortunately. Hope you can help with some advice, thanks!

    • Glad you liked the post Marco, sounds more like you’d be a 10.5 than an 11 or 10? Honestly if the maker doesn’t make your size you may need to move on, no need to spend money on something that doesn’t fit right! But if you’re married to them, yes, a cobbler could stretch out those 10s for you.

  19. Hi Nick,
    Honestly, this guide will keep being useful for years and years to come! Thank you for sharing this with us. I had a hard time finding my size because I live outside the US, so I have to buy online. I think I finally got my size for Goodyear Welted boots, even though there might be some variations depending on the last. My right foot is 9 and the left 8.5 in the Brannock device, so I went down to an 8 in my Iron Rangers, Thursday Captain and Diplomat, as well as my Wolverine 100 Mile (these have a wider toe box though, they feel a bit roomie in the front, but as you point out in the article, it is not a big deal at all).
    Now, I am considering investing in my first Alden “Indy” 405, and I have to face my fears again!!! What could be my size? You see, the problem is that sending back a pair of boots from Panamá is costly, and with the price f the Alden is also a risk! What would you recommend? How did you go with your Alden?

    Cheers mate!

    • I’m delighted this was so helpful, Ely! Aldens are tricky, I originally went true to size but then I got a pair in my Red Wing size and they worked well, I’d recommend sticking to that size. Beware that not every brand fits every foot!

  20. Dear Nick,

    Thank you for the great article. Bought my first pair of IR in a 9. Fitted great.
    Wanted to get a Blacksmith and I thought I would go for a 9 too. Unfortunately, there’s slightly more room at the heel than usual and it kind of disturbs me. Could a 9 in Red Wing be different from pair to pair? Unfortunately the shop refused a return for me as I have worn it a couple of times. Am looking to get some heel pad/grip and hopefully it will help.

    • CL, that’s grazy! IR and Blacksmith are legit made on the same last, it doesn’t make sense they’d fit differently unless it’s a QC problem at Red Wing, which is definitely possible, or maybe it got mislabeled. If you can’t return them, yeah some heel padding or an insole will help.

    • That’s the easiest to adjust with lacing, but if it’s tight on the back of the ankle it usually abates with wear as the leather softens

  21. Thanks for all the tips. This article helped me decide on wether or not to keep my Wolverine 1000 Mile boots. So far so good after keeping all your tips in mind!

  22. Amazing tips here and in all your other articles / videos! Love your collaborations with Rose Anvil.
    One more area of fit I’m wondering about: top of your feet. I just got a pair of Thursday Captains and (due to my orthotic insoles) the boots feels extremely tight on the top of my feet. All the other fit ‘metrics’ are fine. Is that something that can be fixed via sizing up or should I rather try to increase space in the boot with the help of my local shoe cobbler?

    • Hmm tough one. Yes, I think it’s worth asking a cobbler if they can stretch that area if everything else is fine. If they’re new, wearing them for a couple weeks could help too.

  23. I can’t find my correct size in Red Wing Mocs after ordering 3 pairs. They are just so damn big and so damn narrow. Most boots that fit me well in the width seem to have around 100mm width at the ball of the foot. RW mocs have about 92mm in the size 8 and 94mm in the size 8.5.
    I felt like the 8 was a good volume but far too narrow – think vice grip on your foot. I think my toe came up to the 2nd moc stitch towards the end of the boot.
    The 8.5 felt a bit roomy in volume and the heel – like I needed a 3mm insole few mm to make them fit more like the 8. If I went with the 8 EE they may be even wider and looser in the heel and volume than the 8.5 wouldn’t they but would actually give me a nice comfortable width across the ball of my foot.
    I’m not sure whether to give up trying to find my Red Wing moc size and move on to a different boot. I do love the look and that Oro leather though! Thursday 8.5 presidents fit me perfectly out of the box and i’m a 9.5 brannock.

  24. Hi Nick, greetings from Indonesia! Just want to say thanks for this site. I read a ton of your articles and watch your (and Rose Anvil’s) channel prior to getting my first Red Wing (an 875), and thanks to guides such as these I nailed the fit perfectly.

    • Hey Ben! That’s so great the site’s been helpful, that’s why I do this — and terrific work picking the 875 as your go-to! You definitely understand the space.


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