High instep creates v-shaped, rest of fit is perfect, half size up would create a shoe too long, too big and unattractive – shoes by J.FitzPatrick Footwear

There is no right or wrong when it comes to fit. There are objective concerns that should ultimately guide someone to a good fit but overall it is a subjective idea that can be interpreted in many ways. This is why 3D scanning machines will never replace bespoke shoemakers or traditional fitting sessions of good ‘ol fashion ‘trying on’ before buying. Because the machine cannot read the person’s preferences on fit. It can only look at it analytically. And when all shoemakers size 10 fits differently, you know that fit is ultimately subjective. So it is more of a gut feeling type of idea. You know by your personal sensations when the fit is good. Not by measurement or dictation of an idea.

Snug loafer fit

With 17 years of fitting people into shoes, reading fit suggestions online and how they all differ, here are my tips on what I have learned are both the good suggestions and the myths that are overused in the industry.

Things to try to achieve when fitting shoes:


1. If the shoe is leather then always look to achieve a nice, snug fit. That does not mean tight. That means that you feel the shoe all-around your feet, as you would a pair of gloves, essentially hugging your feet. The reason is that leather always loosens/shapes, mainly in the width but also in the footbed (i.e. the insole). If the shoe starts snug, once broken in, will/should fit just right as the leather will essentially mold to your feet. If starting off too ‘comfortable/loose’ then once broken in, it will become sloppy. Sloppy means your arch will start to overwork itself and this, ultimately, is where feet issues start happening.

Don’t be afraid to feel the shoe. It should not be some loosey-goosey feeling when fitting properly.

2. Your heels should have minimal movement. This is more easily achieved in a lace shoe. Monkstraps, loafers and boots will not always be so simple. In these models a touch of play is okay. This will form to your heels after wear and fit better. You can read more about this here.

I always recommend getting chelsea boots, wholecuts, monkstraps and loafers on the snug side. They all break in quickly and usually more significantly due to their pattern styles and how the seams (or lack thereof) lay.

If your heels pop out (in a loafer) or move significantly upwards when in a lace shoe/boot/monkstrap etc then the shoes are too big and you should take the half size down.

3. When your arch is being properly supported you should feel minimal of anything in the arch as it is essentially cupping your arch. When you feel pressure in the arch, like a lump/bump/pressing into it, then the arch is in the wrong spot for you and over time will cause an issue. Always look to feel minimal yet supported (if that makes sense). You should feel like your arch is being hugged without it being prodded. Look for that feeling.

4. It is okay to have excess space in the toes. Most modern-shaped lasts are elongated and your toes should never reach the end. Don’t be afraid of that excess space. As long as the above points apply, the fit will be okay.

5. Dress shoes should always be tried with thin dress socks and worn with them too. Take one with you if you intend to try dress shoes and are actually dressed casually, with thicker athletic socks. The sock weight can change your size by half, at least. Never try dress shoes with athletic socks. You will not achieve the correct fit and size.

6. Always fully tighten the laces or fasten the straps when trying on shoes. If you half-lace them or put the monkstrap on the 2nd hole when you easily achieve the 3rd, you will inevitably feel the shoe loose when it could very well be your size.

Actions/Ideas To Avoid – Myths Often Stated by Others:


1. Never stick your finger in the back of the shoe as an indicator of anything. That is pure rubbish. Stick to my suggestions on heel play when the shoe is fully tightened/fastened.

2. If you have a high instep you will inevitably have a large v-shaped gap in the laces of most oxford shoes. Don’t listen to online commentators that say that this indicates a bad fit. It is easy to make this statement when you have a regular instep and have never had to face this issue.

If this happens to you, could you have a better fit? Yes, of course, through bespoke. So long as the arch, width, and depth fit well and do not hurt you, the instep can be snug at first. You will always fall into the footbed and gain more space and be able to then tighten those laces and thus that gap, after the inevitable break-in period

Try to find lasts that fit your instep better, if possible. But if you fit the rest of the shoe just fine and the instep does not bother you, do not let others tell you that you have the wrong size. It is far worse to size up, to get less of a v-shaped gap yet get a loose feeling everywhere else. And not everyone can afford the luxury of bespoke.

Bespoke Bestetti shoes – with creasing on the caps

3. Creases in the cap area does not automatically mean bad fit (or bad quality for that matter). That is ridiculous. There are numerous factors that can create this issue. Elongated cap toe designs create this. The position of the toe puff can create this. A toe puff too skived (thin) can create this. And yes, a poor fit can ALSO create this but it is not the sole factor.

4. The length of a shoe will never stretch. Never trust a salesman that indicates such craziness. If the shoe is too short in the moment, it will be too short forever. The toe puff makes sure of that.

5. Use the Brannock Device as a starting point but not as the end-all-be-all. You can measure length 10 but shoe size 9 can fit you more comfortably. Go with what feels good. Thats what fit is anyway. Like beds. Some like stuff ones. Some like soft ones. How can one person tell another which is better? They cannot. It’s all a matter of personal preference.

High intep, but solid fit. Shoes by Carmina, courtesy of Shellvedge on IG
V-shaped gap but with good fit. Crushing the myth. Photo courtesy of Armandomadrid on IG
Solid loafer fit, nice and snug. Shoes by J.FitzPatrick, photo by Mes Chaussettes Rouges

4 thoughts on “Shoe Tips Series – Fit”

  1. Did you or, if not, could you address the issue of using orthopedic insert in dress shoes, and how they affect the fit? I use the “Superfeet” inserts on shoes because of plantar faciitis/arch issues. Thanks

    1. Justin FitzPatrick

      I did not as that is not as easy as a subject as all orthotics will be different in shape, size, depth etc and how they fit each different shoe is impossible for me to say as each shoe has various shape, size, depth etc.

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