How Should A Dress Shoe Fit?
Healthy Feet

How Should A Dress Shoe Fit?

There are a lot of misconceptions about how dress shoes should fit. The most common misconceptions suggest that dress shoes should be uncomfortable. Here at Samuel Hubbard, we have a different vision for dress shoes. Follow these guidelines to find a great fitting pair of dress shoes.

Finding Your Shoe Size

Different brands, cuts and styles of shoes will yield very different fits. First, you need to find the right size (length and width) and then you can compare brands and models to find the pair that fit you best.


The most common shoe size measurement is the length, which determines your shoe size. As a shoe gets longer, it will also get marginally wider. As previously noted, shoe sizing varies by brand, so check the manufacturer’s sizing recommendations - some brands will suggest sizing up or down for a particular model.

If you are unsure of your shoe size, you can use a Brannock device to get an accurate measurement. If you don’t have access to one, you can download our printable Brannock device and measure your feet at home.

It’s also smart to double check your shoe size from time to time, especially if you’re investing in a high-quality pair of shoes. Your feet will grow and change as you age, and you may find that you need a half size larger than you thought.

Your Feet Are Different Sizes

When measuring your shoe size, or trying on shoes, remember that one of your feet is probably bigger than the other. This is perfectly normal - it’s estimated that more than 50% of the population have one foot that is bigger than the other.

The difference is usually pretty small and if one foot is a half size, full size or even 1.5 sizes bigger, then you can wear the same pair of shoes - but size them based on the larger foot. It’s better to have one shoe that is a big looser than one that is extra tight.


Shoe width is equally as important as length. While most people are fine with a normal width (men’s D or women’s B), some will need a wide width. Wide width shoes will have the same length as their medium counterparts, but extra room in the toe box and forefoot.

If your shoes frequently feel tight, or you keep the laces loose, consider trying a pair of wide shoes. Even if you’ve never worn them before, feet usually get wider as we age, and you may find that a wide width shoe fits better.

Learn more about wide width shoe sizing.

Trying On Shoes

Trying on a pair of shoes is always the best bet to ensure that they fit correctly, and if you can’t try them on before buying them, make sure you’re buying from a retailer that offers free returns and exchanges. Samuel Hubbard has always had a generous returns policy because we want to make sure our customers are able to find a comfortable fit.

When you’re trying on a pair of shoes, take these factors into consideration.

Try On Dress Shoes In The Afternoon

Your feet swell throughout the day, which means they’ll be larger in the afternoon than they were in the morning. This is the best time to try on dress shoes - when your feet are at their largest. You don’t want to buy a pair of nice dress shoes and then find out they’re too tight after a long day of wearing them.

Wear The Right Socks

When you’re trying on dress shoes, wear the same pair of socks that you would normally have on with the dress shoes. Dress socks are usually thinner than regular socks, which can affect the shoe’s fit. Or, if you plan on wearing thickers socks with your dress shoes, wear those when you try the shoes on.

How A Dress Shoe Should Fit

Here are some common tests to make sure your dress shoes fit properly.

Toe Fit

A shoe’s toe fit can be used to check both the length and the width.

To test the length, put both shoes on, tie them and stand up. With your heel pushed against the back of the shoe, your toes should not touch the front of the shoe, and there should be about a half inch of extra space. The difference between a full shoe size is usually ⅓ inch, so if the fit is close, it’s easy to go up or down a half size to get a better fit.

To test for width, check the fit on your pinkie toe. It should have a reasonable amount of space - if it feels crammed in there, but the overall length is good, you might need a wide width shoe.

Forefoot Fit

Checking forefoot fit assumes that the overall length is correct, and is a strong indicator that you may need a wider or narrower width.

To check forefoot fit, sit down, put both shoes on, and tie them as you normally would. Now pick your feet up off the ground and shake them side to side. The shoes should move with your feet - if there’s excessive movement within the shoe, then the shoes are too loose. Look at the laces - if there’s room to tie them tighter, try that and repeat the shake test. You may need to do this a few times.

If you tie the shoes as tight as you can and there’s still movement, the shoes are probably too wide and you should try a narrow width, or a different model/brand. You’ll know the shoes are tied as tight as they can be when the left and right facing (the leather where the lace holes are) and pulled tight against each other.

If the shoes pass the shake test, stand up and walk around. The shoes should feel comfortable without feeling tight. If they feel tight, loosen the laces and try again. If the laces are as loose as they can be, and the shoes are still too tight, try a wide width.

Heel Fit

Heel slippage is a common concern with dress shoes. Most dress shoes use a stiffer outsole to prevent leather creasing and preserve the shoe’s look. The stiffer sole means less flexibility which causes the heels of your feet to pull out of the shoe a bit with each footstep. Some heel slippage is normal, but an excessive amount is a sign of a bad fit.

You can feel for heel slippage by trying on the shoes and walking around. You can also use the finger test - while wearing the shoes, try sliding your index finger between the heel of your foot and the heel of the shoe. You should have some difficulty - if your finger slides in easily, the shoes are too big and there will be too much slippage. If your finger is impossible to fit, the shoes are too tight and will cause chafing or blisters.

Do Dress Shoes Stretch?

Leather dress shoes will stretch a little. Leather has a break in period where it will conform to your feet. In terms of sizing, leather stretching shouldn’t have much of an impact. A brand new pair of shoes shouldn’t be too tight or too loose. If you’re perfectly in between a pair that are a little too tight and a little too loose, the tighter pair may stretch out just enough to be perfect.

To preserve the shoes’ look and durability, stretching should occur naturally. Wear the shoes around the house to help break them in - thicker socks can help with the break-in process. Excessive stretching with tools or heat is never a good idea. It’s an immediate sign that the shoes don’t fit well, and it’s likely to damage or wear out the leather prematurely.

Shop Dress Shoes From Samuel Hubbard

Samuel Hubbard’s men’s leather dress shoes are handcrafted in Portugal, using the finest materials available. Shop our selection of super comfortable suede and leather dress shoes.