How Should Your Shoes Actually Fit?
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The Wall Street Journal’s senior style reporter Elizabeth Holmes recently started her column by asking a simple question: “When was the last time you had your foot measured to check your shoe size?” I promptly answered in my head and also possibly aloud, “Well, when my foot last stopped growing. Why would I need to do it again? I’m a grown adult human who pays the majority of my bills on time. I think I know how to buy and wear shoes.”

Apparently not. Holmes’s article goes on to explain how our feet have grown an average of two sizes since the 1970s in order to support us as the species grows taller, which is changing how shoes are designed, made, and sold by older, established brands. She also cites a recent U.K. study of more than 2,000 similarly grown adults, which proves that while sitcoms and stereotypes suggest it's women who choose style over comfort, about a third of men are also wearing shoes that don’t properly fit them; a choice that's not only uncomfortable, but can actually deform your toes and feet over time. Shit.

So after trying on every pair in my closet, many of which are curiously worn out in the same spot on the outside of each foot, I asked the experts how our shoes should actually fit.

“Generally you should have about a half-inch of space between your longest toe and the leather of the shoe,” says Tom Florsheim Jr., CEO of his family’s 122-year-old brand. “Your foot shifts when you stand up, so you want to ensure it fits while you’re on your feet.”

Pinching the toe is a common practice, but Florsheim suggests you also slide an index finger behind your heel. If it doesn’t fit, go a size up; if it slides into the shoe easily, you should probably drop a half- to full-size. Even then, some stores will try to make the sale by convincing you that, while the shoe might feel tight, it will stretch and break-in as you wear it. And that's true, but only barely, and something you should never rely on.

“If a shoe isn’t comfortable to begin with, it is never going to be,” Florsheim adds. “Shoes stretch in particular ways that are predictable because of the way your foot moves, but changes will be marginal. And do not expect the shoe to stretch length-wise.”

Regardless of how long you’ve been buying and wearing the same pair of shoes in the same size, if you want the best fit, you should get your feet measured in store about once a year. "Your foot changes throughout your lifetime, so it is always good to get it correct when purchasing new shoes," adds Brad Hren of Ben Sherman footwear. 

It might take an extra few minutes to corral someone for help, but shoes that fit correctly will also last longer, feel better, and generally improve your way of life each day.

“A shoe should always feel as good as it looks. Otherwise it’s not worth the purchase."

Six more tips for buying your next pair of shoes:

1. Wear the same type of sock to the store that you’ll be wearing with the particular shoe. A thick white tube sock or thin dress sock can sway the fit more than you think.

2. Width is often as important as length, so make sure the shoe fits in every direction.

3. Shop for shoes at the end of the day when your feet have already expanded.

4. If you fall in love with a pair that's slightly too big, try them on with insoles. 

5. If your feet are different sizes, make sure to measure the larger one for best fit.

6. If you’re not sure about how a particular brand fits when purchasing online, don’t be afraid to buy two and plan to send one back. At this point, shoe companies are almost counting on it, so return shipping is usually free.