Shoe horn in brown dress shoe

This article explains what a proper shoe fit is, how feet are measured for ready-to-wear and bespoke shoes, how to make shoes fit better, and more. If you’re looking for information on shoe styles, see our shoe style guide. Information on sizing including a full, international size chart can be found on our sizing page.

It’s almost funny to be talking about how a shoe should fit. It’s perhaps more understandable that a man wouldn’t know how a suit is supposed to fit, as there are plenty of men who wear them rarely enough to justify the lack of knowledge.

Shoes, though? Everybody wears shoes, everyday. How can there be confusion on such a ubiquitous, widely-understood topic?

Wearing shoes may be ubiquitous, but achieving a proper fit is by no means widely understood. Below, we’ll get into the nitty-gritty details of how your shoes should fit on your foot.

Proper Shoe Fit

finger in heel of penny loafer

Say it with us, gentlemen: there is no reason that shoes shouldn’t feel as good as they look. While your foot “knows” when a shoe doesn’t feel right, an inability to articulate precisely what your issues are can make buying them difficult. Here is a quick hit list of things you need to know about how a shoe is supposed to fit:

  • Unless you’re going fully bespoke (more on that below), shoe sizing is two-dimensional and accounts for length and width. We have in-depth information on the actual measurements on our sizing page, but as it relates to how your foot feels, there should be 3/8″-1/2″ of space between your longest toe (often the second toe as opposed to the big toe) and the end of the shoe’s toe box. This is particularly true with shoes made on tapered or pointy lasts as opposed to rounded ones, but the rule applies regardless.

See the picture below. This Allen Edmonds penny loafer is a properly-fitted shoe, but you can see that its length is a fair amount more than the length of the foot beside it.

foot inside and outside of shoe

  • On the other end of the shoe we have the heel. There are generally two ways to determine if the shoe’s heel syncs with your own:
  1. You can fit your forefinger between the shoe’s heel and your own, but nothing more, and /or
  2. Your heel doesn’t slip inside the shoe when walking, nor is there any uncomfortable rubbing or pinching.
  • If you tell a salesperson that the shoes feel a bit snug and (s)he tells you that they will stretch, do not listen. While it’s true that leather softens and gives over time, it will never stretch out enough on its own to make a tight shoe fit properly. With that said, cobblers and some shoe stores have the ability to stretch shoes on proper shoe stretchers, but this is far from a scientific process and should only be done if you’re talking about a pair of shoes you absolutely cannot live without.
  • The thickness of your socks matter in a big way. If you’re shopping for dress shoes but wearing athletic socks, you will definitely not get a proper fit. The same goes for wearing dress socks when buying sneakers. When you go shoe shopping, wear the type of socks you plan to wear with the shoes you’re buying.
  • Shoes’ width is incredibly important when achieving the correct fit. A great rule of thumb (or toe, in this case) is that the ball of your foot should sit at the widest part of the shoe. Bear in mind that the number of retailers offering non-standard widths is decreasing. Allen Edmonds is one of our favorite brands, and a reason for this is that they offer an incredible range of sizes and widths for most of their shoes.
  • As often happens with body parts that come in pairs, you are likely a bit asymmetrical or irregular, and this means that one of your feet is likely a bit larger or smaller than the other. This isn’t to say that they’re totally different sizes, but this isn’t unheard of. It may seem obvious, but we’ll say it anyway: accommodate the larger of your feet as it relates to your shoe size.
  • Have your feet measured about once a year. You’d be surprised how much things can change over time.
  • Sizes and widths are guidelines, not rules. One brand’s 10D can fit totally differently than another’s, so do what your foot tells you, not what an arbitrary size says. Further, if you’re ever in doubt about a size, go by what’s stamped inside the shoe, not what’s written on the box. Mistakes happen.

Side Effects Of Poorly Fitting Shoes

We don’t typically engage in scare tactics, but you should know that the side effects of wearing poorly-fitted shoes are not fun at all. Some of them are:

  • Bunions
  • Corns
  • Calluses
  • Pain/discomfort
  • Stress Fractures
  • Plantar Fascitis

If it turns out you suffer from some of the above afflictions, you may want to explore getting custom orthotics designed by a podiatrist.

Ways To Make Shoes Fit

insoles in and out of a shoe

Sometimes a pair of shoes fit is very close, but not quite there. While we always advise that you only buy shoes that fit well, sometimes there are shoes that are too gorgeous or too good a deal to pass up. In such cases, you can finagle the fit using certain products and the effect is similar to making alterations on clothing.

  • Insoles: If your shoes feel a bit too big, the first thing to do is put insoles in them. Many shoe stores have them in stock and will offer them to you gratis, and just about any drug store will sell cheap ones that do the trick, such as Dr. Scholl’s.
  • Heel Grippers: If the shoe fits well but slips a bit in the heel, try a hell gripper. Adhesive on one side and grippy on the other, you simply adhere it to the inside of the center of the shoe’s heel. It can take up just the right amount of space to make your shoes fit perfectly.
  • Felt Pads: Every once in a while, a shoe fits decently but literally rubs you the wrong way. A strategically-placed felt pad will often give you a night-and-day experience as it relates to this, but note that it may make the shoe feel every-so-slightly tighter. Note that moleskin is available on the market for this purpose; in our experience, it doesn’t work nearly as well as felt does.

felt pad for shoes

  • Stretchers: If a shoe is too tight, they can be stretched on wooden stretching devices that resemble shoe trees. There are two types of stretchers: one that stretches width, and another that stretches the vamp upwards. The latter is typically used on slip-on shoes as their fit can’t be adjusted by laces or buckles.

To reiterate, stretching shoes is a last resort measure that we don’t typically recommend. But, as we mentioned above, sometimes a pair of shoes just speaks to you and you’ll do anything to have it!

Bespoke Shoes

Blue Tassel Loafers On GrassOur discussion up to this point has centered around ready-to-wear shoes, which account for the vast majority of shoes sold on the market. Made-to-order shoes from brands like Undandy are becoming increasingly popular, but they still use stock sizes and widths in the same way that ready-to-wear brands do.

What about fully bespoke shoes and how they fit? Further, are you a good candidate for them?

As we mentioned earlier in this article, most shoes are measured with two dimensions: length and width. Bespoke shoes, on the other hand, add a third dimension: height.

Bespoke shoes will typically be much more expensive and take more time to create than their off-the-rack counterparts, so the expectation around fit is much more exacting. As is the case with bespoke suits, every curve, nook, and cranny of both of your feet are accounted for. While the shoes will still require some breaking in, the idea is that they will fit you perfectly right off the bat and will last for many, many years.

That’s great and all, but does it make sense to buy bespoke shoes as it relates to fit?

If your feet and shoe size are reasonably straightforward, then the answer is no. Bespoke shoes are quite expensive and while the cost may be worth it to you from a design perspective, the value is lost on fit if you don’t have any serious fit issues.

On the other hand, if you have serious fit issues such as a foot deformity or two different sized feet, investing in bespoke shoes starts making a lot of sense very quickly. Unique lasts will be made of your feet, which means that the shoes created form those lasts will accommodate every last one of your feet’s idiosyncrasies. For a guy who just can’t fit into ready made shoes, bespoke ones alleviate that pain point.


Ensuring a proper shoe fit will make your shoes last longer and keep you more comfortable while you’re wearing them. A poor shoe fit, on the other hand, will make your life miserable and can wreck even the best pair of shoes.

If you need more information on shoe sizing, take a look at our sizing guide.