in: How To, Skills, Visual Guides

• Last updated: May 27, 2021

How to Choose Shoes That Fit Perfectly

Shoe shopping may not top many men’s lists of favorite activities, but from time to time, it has to be done. And it’s a process that should be done with a bit of care. Beyond the style considerations that may be foremost in your mind, your shoes will have a disproportionate influence on your overall comfort level. Ill-fitting shoes can make standing and walking a literal pain, and cause significant health issues for not only your feet, but your ankles, knees, back, and more.

So whether you’re buying casual athletic sneakers or formal dress shoes, you want the pair you choose to fit as perfectly as possible. Following the guidelines outlined above will get you much of the way there; following these additional tips will bring your new kicks on home:

1. Try on shoes in the afternoon/evening. Your feet will swell during the course of the day, and it’s better to have your shoes fit your feet at their largest, than at their smallest.
2. Try on shoes while wearing the kind of socks you’ll normally be wearing with them. If you’re going to be wearing dress socks with your dress shoes, try on dress shoes with dress socks. If you’re going to be wearing athletic socks with your athletic shoes, try on athletic shoes with athletic socks.
4. When you go to try on shoes, don’t get overly stuck on “your” size. Don’t do your shopping with the mindset: “I’m a size 10, and these shoes are a size 10, so they should fit.” While you may typically be one size, every brand’s shoes are sized a little differently. So start by trying on a pair with your typical size, and then go up or down in size, depending on how your foot feels, not what the number on the shoebox says.
5. Always try on both shoes. One of your feet is often larger/smaller than the other. Buy the size that fits your larger foot.
6. Do a test walk on both hard and soft surfaces. Different surfaces will give the shoes a different feel. 

7. Make sure they feel good right out the box. While new shoes will conform to your feet with regular wear, especially if they’re made from leather, the degree their size and shape will change over time isn’t significant. So don’t count on this breaking-in process turning an uncomfortable, ill-fitting shoe into a comfortable, well-fitting one; your shoes should feel good and fit well from the get-go.

Illustration by Ted Slampyak

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