Men's Clothing Fit Guide

How Should Shoes Fit?

This article is part of my Men’s Clothing Fit Guide.
When I’m fitting my clients in sneakers or casual shoes for the first time, they can easily tell me when shoes are too tight or too loose, but outside of the super obvious, they have a hard time figuring out if they fit properly or not. So I came up with two ways to tell if their shoes fit properly or not. 

the one finger test

Try on the sneakers while wearing a pair of socks you’d normally wear with your sneakers (please, lord, they better not be WHITE SOCKS!) and insert your index finger between your heel and the heel of the shoe.

It should be pretty snug but not so snug that it smashes your finger and is painful. If your finger can’t move without considerable effort, the shoes are too tight and you need to go up a size.

If you can freely move your finger without really touching either your heel or shoe, they’re too big and go down a size.

Squeezing or Pressure on Sides of Feet?


If you feel any squeezing or pressure on either side of your foot, the shoes are too small or narrow. There should be no squeezing sensation on any side of your foot if the shoes are fitting properly. If this happens, you should go up a size and see if that helps. If it doesn’t then you may get lucky and the brand makes a wider size, but for sneakers/casual shoes that’s very rare. If they don’t have wide sizes, you’re going to have to find another brand that fits you better.

But Won’t Sneakers Stretch?

I’ve heard this argument a few times from clients. Yes, but it will be very little and will not be enough to go transform them from uncomfortable to comfortable. If you buy sneakers (any shoes, really) thinking that they’ll fit once you’ve “worked them in”, you’re going to have a bad time. Sneakers should fit the second you try them on. If they don’t, they’ll never fit comfortably.

What are the Best Sneakers/Tennis Shoes For Men?

Check out my Men’s Wardrobe Essentials – The White Sneaker story for details about my favorite pairs of sneakers that every man should own.

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