How Should Dress Shoes Fit? | Learn What to Look For

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Many people struggle to find proper fit dress shoes that are comfortable, affordable, and stylish.

They seem to associate discomfort with wearing dress shoes when in truth, you can actually learn how dress shoes should fit to save your feet from pain and blisters. Plus, getting dress shoes that fit you properly can extend their life, which means you don’t have to keep buying new shoes every few months.

How Dress Shoes Should Fit and Tell-tale Signs That They Don't

There are some telltale signs that your shoes don't fit you properly. Maybe the footwear you’re wearing isn’t the right size for your feet. Knowing these signs will help you determine whether you'll need to start to shop for new shoes soon:

  • Creasing in the toe area is a big sign that you're wearing the wrong sized dress shoes. Since it doesn't fit correctly, your foot is bending in an unnatural way, which leads to cracks and creasing on your shoes
  • Constantly tripping while walking is an indication that your shoes are too big for you. Your dress shoes should feel like a part of your feet and walking should feel natural
  • The widest part of the shoe is not aligned with the widest part of your feet is the most significant indication that your shoes are not the right size. If the balls of your feet are not slotted on the widest area of the shoe it can cause a lot of blistering and discomfort. Double check that your feet and shoes are perfectly aligned before buying them to avoid any pain
  • Flopping feet inside the shoes means that you're wearing dress shoes that are too big for your feet. They may not cause pain like a too-small size pair of shoes, but they can still be uncomfortable to wear. 

Tips to find the best fitting dress shoes

Now that you know what signs to look out for to know that your shoes don't fit you properly, here are some tips you should consider when shopping for a new pair of dress shoes:

How to shop for dress shoes

Know the general size of your feet

Shoe manufacturers don't always have a standard sizing chart, which means you can have different sizes depending on the brand of shoes you select.

Although this can be a challenge, you should already have a general idea on what size shoes you wear so you'll have a ballpark figure when you go shoe shopping. Many companies also offer size charts, which come in handy.

The perfect fit the first time

Most dress shoes are made with leather, a material that doesn't stretch a lot. If the shoes you buy don't fit you properly from the get-go, it's doubtful they'll fit with usage.

Try them on to see if they pinch; if they do, you’re better off with a bigger size.

Buy shoes in the afternoon

Your feet expand throughout the day and buying shoes, or measuring your feet in the afternoon gives you a better idea of how big your feet really are. This leaves room in the shoes you choose for your feet to expand during the day.

Are both your feet the same size?

It may come as a shock, but both your feet are seldom the same size. One foot will be slightly smaller than the other, and knowing this will help you know how dress shoes should properly fit.

Get the shoe size that accommodates the larger foot so that both feet will be comfortable.

Try shoes on with socks

Wearing dress shoes without socks is uncomfortable and unhygienic, so you have to take into account the space your socks will occupy. Try your dress shoes on for the first time while wearing a pair of socks you typically use.

This will give you a precise estimate of whether the shoes are still comfortable, even with socks on.


It's a myth that all dress shoes are uncomfortable and painful to wear. If you know what to look for when shopping for dress shoes, you'll find a pair that's comfortable to wear the entire day.

Last Updated on November 5, 2021 by admin_comfortabledressshoes