3 Steps To Find The Perfect Fit For Men Formal/Casual Leather Dress Shoes

The biggest problem with buying formal/casual leather dress shoes is finding the right size.

80% of men wear the wrong size shoes according to Master Fitter, Ryan Stowe from Allen Edmonds, a renowned US shoe brand.

Fit is king and this applies to shoes as well.


Dangers of wearing the wrong leather dress shoe size

Wearing the wrong formal/casual leather shoe size can cause discomfort - blisters, fatigue, etc

But in the long run, more serious feet conditions like bunions, plantar fascitis, corns, etc can develop.

The number of men that walk in my office with these feet conditions are quite high. Most of these conditions can be attributed to poor shoe fit.   

At CustomMade, we have our expert fitter, Cecilia and myself who fitted more than 600 shoes and a 14 step fitting process to ensure we find the best fit for you.

So let me just share a bit on how to find a perfect fit when you're going shoe shopping.



When was the last time you measured your feet?

If like most men in Singapore, i would say never. So that means you don't even know what is your proper feet size.

You cannot get a good fit without knowing your feet size.

A brannock device is for measuring feet length and width (outstep) - widest part of your feet

There are two parts to your feet size: the length and the width.

The length is measured by numbers, US 9, UK 8 or Eur 43, etc

The width is measured by alphabets, D, E, EE, G, etc (as the alphabets advanced, the wider it is) 

So your feet size should contain both aspect. E.g. US 9E or 10G

With the length and width, only then can we begin to find a good fit.




Choose the closest to your feet size the brand has to offer.

Put on the shoes and stand naturally, shoulder width apart. Always stand up as your feet would expand and put pressure on the shoes when you stand.

Always remember, width is more important than length. Always.

Majority of discomfort for fit is caused by the width, not the length.


  • Look down at your feet. Does it run over the sides?

If so, the width is too tight. Go up a size.


  • Does your pinky toe/big toe pinch on the walls of the shoe?

If so, go up a size

  • Wiggle your toes a little. Does the toe box have enough room?

If not, go up a size

  • With your heel on the ground, flex your toes upwards once. Is the crease perpendicular to the widest part of the shoe?

If it's above, it is too tight. Go up a size. Vice versa.


  • Use your own fingers to feel your outstep (widest part of the feet). Is it at the widest part of the shoe?

If it is not, size up or down until it matches. The widest part of your feet should match the widest part of the shoe. 


  • Can you snugly fit one finger in the back?

If you can't, go up a size. If it slides in too easily, go down a size.




Majority of the fit should be done in step 2. If step 2 is done right, this is more of a confirmation.

Take about 6 to 7 steps on your shoes.

  • Does it affect your balance?
  • Does the heel slip off too much?
  • Is there anything off?

The answer should be no to these questions.

If you answered yes to one of these questions, you have to go back to step 2 and assess which size to change to.


Dress Shoe Styles And Fit


Shoe Fitting Video From Allen Edmonds




The biggest problem with shoe fit is that you do not know what a good shoe fit is.

How much heel slip is too much?

What is the difference between a good snug width fit and it being too tight.

Compound that with the fact that you're only wearing the fitting shoes for a minute or two, not nearly long enough to know it is a good fit.

Especially if you lack experience or knowledge. it is no wonder most men get a bad fit.

The best solution is a fitter and a fitting process. A good shoe fitter would know his own brand's shoe sizing and widths.

Together with the customer's feet measurement and the fitting process, he can recommend the best fit.

It saves you the trouble of even understanding shoe fit. None of my customers need to understand what a good fit is to get a good fit. Because I do.

That's the whole point of a fitter and a fitting process.



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