How To Tell If Shoes Fit

How To Tell If Shoes Fit

how to tell if a shoe fits

As a logical follow up to my mention the other day of a piece I wrote for Business Insider on shoe brands under $350 I would like to talk about how to tell if your shoes fit you properly.  Which, to be honest, is not much different for men than it is for women.  Additioanlly, keep in mind these bits of advice are equally applicable for shoes costing less than $350 as they are for those well over $350.

As I am sure we all know, wearing shoes that don’t fit well or that are uncomfortable can ruin a day.  Many days, in fact.  I remember in the days before I gained a proper appreciation for well fitting footwear I would develop blisters on parts of my feet meanwhile other parts would be sore or tender after a long day of wear.  It would distract me from my work and have an adverse effect on my mood.  It was no way to go about things. But a few years of trial & error and research into the subject has taught me a few important things which I would like to share:

how to tell if a shoe fits
Allen Edmonds, Brooks Brothers, Just A Man Shoes, J. Fitzpatrick, Gary Michaels, Meermin

1. Although the last is the physical form for which a shoe is constructed around (literally) it is also used to refer to the shape of the shoe.  In short, the last used in making a shoe determines the toe shape, heel shape, toe box volume, instep height etc.  The first time you put on a shoe, it is either comfortable or not comfortable.  It should be snug, not tight and not spacious.  Yes the leather plays a role in this.  But it is largely due to the shape of the last and how well it fits your foot.  And some lasts just won’t fit you.  There is only so much you change on the feel of a shoe while breaking it in; some shoes will just never be comfortable (take for instance the photo above, all of the shoes are a US10 or UK9, which are equivalent sizes, note the differences in length, width and toe shapes; these are due to the lasts being different shapes).  If women realized this, we would see far fewer of them carrying their shoes down the sidewalk while walking barefoot at the end of the night.

2.  The last of a shoe has little to do with the quality of the shoe.  You can find a shoe made on a last that fits your foot very well for $150 and then a last for a $500 shoe that doesn’t fit well at all.  If you find a last(s) that fit you well, ask the brand(s) what other styles they make on that last and look to those for other options.

3.  A shoe’s leather will often expand and widen with wear, albeit only a little bit.  However, the shoe will not get longer.  If your toes are crunched at their tips, don’t expect that to get much better with wear; you want a little bit of space between the ends of your toes and the end of the shoe.  Either go up a half size or admit that the last doesn’t fit your foot and find another shoe no matter how much you like the styling of that shoe.

4.  Wear the type of socks when trying on the shoes that you will normally wear when wearing the shoes.  In other words, don’t wear ski socks when trying on dress shoes.

5.  Know your shoe size, which is usually obtained by using a Brannock Device (pictured above).  But keep in mind that this is not an absolute.  In one brand you may be a 9 and in another a 9.5.  Don’t be afraid to try other sizes.

6.  Know that US, UK and European sizings are different.  And that the conversion scales that brands use may vary.  I have found the best luck in following each brands conversion scale.

7.  Make sure the ball of your foot sits well in the widest part of the shoes, as the ball is the widest part of your foot.

8.  Take note of how your heel sits in the shoes.  If it slips out when trying the shoes on chances are this will not get much better, especially with a loafer.  The sole becoming more flexible with wear will slightly alleviate this problem but the real root of the problem is that many shoes have too wide of a heel to begin with which goes back to my first point about lasts.

9.  Walk around in the shoes before buying them, obviously.  But take it a step further and once you have the shoes home, walk around in and wear them for a few hours on carpet or surfaces that wont scuff the sole of the shoes.  This should give you a better feel for the shoes than putting them on briefly in a store; or if you purchased them online then this is a must do step.  Often shoes are not returnable once the soles are marked or scuffed.

10.  Nearly every person’s left and right feet are different sizes, often the difference is less than a half size so there is rarely an issue.  Regardless, fit the shoes to your larger foot.  For those with over a half size difference, some brands and stores may let you mix and match sizes or custom order two different sized shoes.

11.  Shop in the afternoon, or at least a few hours after your feet have had a chance to warm up and expand, as your feet will become slightly bigger as the day goes on.  This fact explains why sometimes when you put shoes on in the morning they seem fine and by day’s end they are tight on your feet.

If you have any questions or tips of your own feel free to sound off in the comments.



  1. Also be aware that your feet may become slightly longer as you age ( gravity or something?) this is only anecdotal and I have no examples to show of double blind scientific trials but my shoe size has gone from UK size 8 to 8.5 in recent years.

  2. Justin,

    Great write up. I have a pair of Cole Haan ankle boots that seem to fit perfectly – snug but enough room in the toe – but by the end of the day, my foot hurts. Makes me wary about the brand in general, but I’ll have to try a different style before writing them off altogether.

    Is it safe to assume they use the same last style for similar shoes? Like all of their chukkas would be the same, all of their loafers, etc.? Or is there no correlation?


  3. Great article. How much will a good quality leather “stetch?” I just got To Boot New York oxfords that I love. On my wider foot, they are a bit snug in the center…in other words my ball of the foot feels like the big toe and pinky toe are being pushed together too much.

    This is slight, and the salesman said it will “work itself out.” Is this BS? More importantly, how long do I wait to tell if it is going to happen?

    • Steve,
      A shoe will stretch in its width but not length. The amount of stretch depends on the type of shoe and the leather. For instance, a moccasin will stretch more than a good year welted shoe. It may indeed work itself out but it is hard to say without seeing the shoes and exactly how snug they are on your feet. So they very well may not stretch enough. Either way, it will take a good bit to break them in, maybe a dozen wears?

  4. Hi,

    I have a question on fit. So I’m trying on a pair of double monks and it’s snug on the instep, toes are secure but not pinching, but there is a little gap/space around my ankles. Do you think that it is acceptable or would you want the ankle to be more secure?

    • Wayne,
      It sounds like the shoes fit decently well. I often find that with off the rack shoes there is a little extra space around the heel and ankle. The reason being is that brands keep that part of the shoe wider to accommodate wider feet, as to not alienate those with wider feet with narrower heels. If you foot is slipping out of the shoe or it is plain uncomfortable then the fit is off. Being snug in the instep is a good thing so sounds like you may be okay.

  5. I am a womens 11.5 . the line. I cannot find women’s shoes that fit!!! Why do shoe company stop half sizes at a 10!

  6. I have a Emerson Crust Quebraco size European Size 44. They are narrow toed. I have about a full inch of space at the toe, is this too much? I am not sure if a 43 would be too small since the toe is narrow. Any thoughts? Thanks!!!

  7. I’m looking for some advice on shoe length. I bought some shoes online and they fit well in all the ways described but there is almost a full inch and a half of extra length in the toe box. Is that a problem? Growing up, my mom always told me that there shouldn’t be more than half an inch. I love the shoes but I don’t want them to look like clown shoes once they have creases Here are some pictures:

    • I have a similar question. I bought a pair of dress shoes a while back (size 10.5) that I thought fit me well, but maybe turned out to be too long. Eventually a crease formed near the tip of the toe where I had been walking. I bought a new pair recently and decided to get a size 10. Turns out this brand of shoes at a size 10 were even longer than the size 10.5 I bought! So I exchanged them for a full size down at 9 and they still feel a bit too long! Like the length didn’t decrease at all. I would there’s about a 3/4 inch between tip and toe. I just don’t want the same thing to happen to these shoes as my old one.

  8. Hello,

    I’ve just got some new Moc Toe style boots, the right shoe fits and feels fine, but the left shoe feels like my small toe is being “separated” out from my toes, and the outside of my big toe seems to rub on the side of the shoe.

    But if you feel the shoes when I’m stood up, there feels plenty of room available all round and that they should feel fine.

    Whats going on here?

    Cheers, Chris.

  9. Hello, I am 6’8 1/2″ weigh 245lbs my shoe size is 12.5. My feet hurt after standing or walking. My feet have hurt since I was 10. I have tried athletic shoes, high top boots, low top boots, lace up shoes and crocs. Nothing seems to work. I have tried custom orthotics and store bought orthotics. Been to 2 podiatrists and they just guess with the orthotics. I am at my wits end. Everybody says you’re feet are too small for your body. Where do you find a shoe store to fit people any more. Help


  10. Great article! I’m a woman and I agree that we know little to nothing about shoe construction, we just focus on the aesthetics…
    Most women’s shoes have paper thin soles. I purchased some boots with leather double soles and Goodyear wetting – now I am having second thoughts. The soles are VERY stiff, which makes the boot feel odd when walking, and the bottom of the ball of my foot hurts. Will this type of sole ever break in? I’ve only tried them on in house and walked around on the carpeted floor a bit.
    Thank you, any advice would be greatly appreciated!

  11. I am interested in purchasing a pair of Stow Country boots. I tried a pair of Bostonian shoes on in the store, they are made in India and the US size is 9W and UK size is 8H. Are Bostonian shoe sizes compatible with Tricker’s sizes or are Tricker’s widths wider than Bostonian? My foot length is 11″ and width is 3 7/8″.

  12. My husband never has time to go to the store and hesitates to order shoes online. I’m sure that he would appreciate these 11 steps would really help him out. Hopefully, I can get him to finally throw out those worn out sneakers he’s always wearing.

  13. I just bought a pair of Doc Marten chukka boots that fit comfortably but I do have a bit of room in both the heel and toe area. Not enough to cause slippage in the heel or to feel my toes moving around, but Im curious if a pair of cushioned boot socks would help with this. I don’t want anything too think but am open to any recommendations you may have. Thanks Joe M

    • Joe,
      A thicker pair of socks may certainly help. That said, if the shoe is comfortable and your heel isn’t slipping, if you can wiggle your toes, thats not a bad thing. The last shape on DMs is usually pretty voluminous so that makes sense.

  14. Hi Justin,

    I recently bought AE St. John’s monkstraps 6.5E. The fit width and lengthwise is good, but on the lacing area, there is some space between the leather and the top of my foot. I’m flat/wide footed. I double checked my measurements on the AE brannock print out and looks about right.

    Any advice? Maybe insoles would help close the gap?


  15. I wore a pair of loafers for a half an hour at the store. I shopped around noon. At five, I tried them on, same socks. The right instep on these suede shoes feels tight. I hope it loosens up, but I don’t understand why. Is it the walking surface? Sounds stupid, but dies softer carpet bring out sizing problems?

    • Peter,
      Small chance your foot could’ve swelled in the few hours between wears. I don’t think the surface you were walking on would do it. If it is not either of those things, I am not totally sure what it could be.

  16. The widest part of your foot should be the end of the toes, not the ball (but isn’t for most people, because they cram their feet into shoes with too-small toe boxes)