How should dress shoes fit?
This is a simple question, but not an easy one. Many people don’t know what to look for. Since dress shoes are structured, it may use a different approach than sneakers. Some reports indicate that up to 80% of men wear the wrong shoe size. 80%. Let’s discuss what to look for so you find yourself among the knowledgeable members of the group.
Before we discuss fit, a quick note on sizing. Size is just a number. Each manufacturer has a different understanding of what standard width means. For example, how a 9D should fit. Different shoe lasts have different fits.
Not every manufacturer uses the same sizing method. North American and British shoes have different sizing. 9 in North America is usually 8 in the UK. Subtract 1. In Europe, number 9 is number 42. The chart below shows the most common widths and sizes. These are not 100% set in stone as every manufacturer is slightly different. Some manufacturers consider 13 North America to be 46. Some say 47.
That means the size of your shoes doesn't matter. If you wear a size 8 from one manufacturer, you may need a size 9 or 7 from another manufacturer.
Regardless of the number inside, here are three things you should look for in a well-fitting shoe:
1. Is the widest part of my foot aligned with the widest part of the shoe? Is the width comfortable?
Sometimes you hear things like, “Should men’s dress shoes be long?” This has to do with how much room there is at the end of the shoe near the toes. Unlike most sneakers, your toes rarely reach the end of the shoe. That's no problem. As mentioned above, this depends on the last your shoes are built on. This will depend on the shape. Many more formal shoes are longer and more "pointy." Your toes will be further away from the finish line. Sometimes 1 inch/2.5 cm or more.

The most important thing is width. The widest part of your foot should line up with the widest part of your shoe. The "ball joint" or "knuckle" (metatarsophalangeal joint) of the foot should sit comfortably in the shoe.
If you put your shoes on and find that your feet are too far forward or too far back in the shoes, the shoes may not fit properly. Many people try to size up to increase the width of the widest part of the shoe. This sometimes works, but usually doesn't. The width you gain will also increase the length. This extra length may mean your foot isn't positioned properly in the shoe.
If you find that your shoes are too narrow, the answer is usually to increase the width or replace the last. Standard men's shoes are D width in North America and E width in the UK. North American width is increased by moving to the letter E and then adding more E's. In the UK, going up a letter usually means going up a width, and more than just an E. Note that this varies from brand to brand, so make sure this applies to the shoes you buy.
North American example: 9D width is the standard width in the United States. The 9E width is the same shoe but wider. 9EE will be wider. 9EEE would be wider. etc. Allen Edmonds is a company known for producing shoes in a variety of different widths. For narrower ranges, the opposite is true, except stopping at A. Please see the image below for reference.
UK example: Width 9E in UK sizes is standard. 9F is wide format. 9G is wider. 9H is wider. For narrower ranges, the opposite is true, except stopping at A. Please see the image below for reference.

Are the shoes stretchable? Yes and no.
The shoe will stretch slightly and relax across the width near the toes. Part of this is because the leather gives way to your foot slightly and becomes larger. This is also caused by pressure on your feet and wear and tear on the midsole. As we said above, midsoles are usually cork or leather. As they wear, they become compressed. This compression will increase the volume available in the shoe. So your shoe feels a little roomier. It will only stretch a small amount. If you put the shoes on and they feel like a vise, they won't relax as much. You should expect to do a very small amount of stretching. If they are very tight, choose a different size or last. Life is too short for painful shoes.
The length of the shoe will not stretch. If you feel your toes touching the end of your shoe, give up immediately. There are structural elements inside the heel and toes to prevent stretching. Shoes that are too short will almost never fit you. Find something else.
Therefore, if the shoe is too short, choose a larger size. If the shoe is the right length but too tight at the toe, you can increase the width.
Note that when you increase the width, you will provide more room for your toes. Whether you like it or not, you'll also have more room in your heel. This brings us to our second point.
2. Does my heel feel safe in the shoe? Or do you feel like you are slipping when you walk?
You want your heel to fit snugly and comfortably in the shoe. If the heels of your shoes are too tight, they can bite or pinch your feet throughout the day. This can cause a lot of discomfort and possibly even blisters. The heel does not stretch, so this may be permanent.
If your heels are too big, you'll have the opposite problem. More commonly, this is called "heel slip." This is when you find your heel slipping out of your shoe while walking. The range can be a little bit (a few millimeters) or a lot (your foot fully extended).
A slight slip on the heel is enough. When the shoe is new, it is the hardest. Midsole and outsole are fresh and unworn. They are not fully bent yet. This means they will bounce back to the neutral plane position with as much force as possible. Imagine stretching a brand new rubber band. So when you walk and bend the shoe, it snaps back into place and wants to flatten.
This effect will lessen after the shoes have been worn for a period of time. Think of old rubber bands. So now the shoes are more compliant. It has less counterattack.
So if your new shoe has very little heel slip, it should decrease over time.

If the heel of your shoe is constantly slipping, it's likely that it doesn't fit well. You should consider reducing the length and/or reducing the width. If you can't do either of these because of your toes, it's time to look for a different last. Different shoe lasts will have different heel shapes. Find one that works for you. For example, the Alden Barrie last is known to accommodate the width of the toe without a lot of room in the heel. Many people say this is the last one they are most comfortable with. As always, it depends on your feet.
3. Are the shoes comfortable?
Is it simply comfortable? Do you think you could walk a few kilometers in these? Are you happy to have them?
If the widest part of your foot lines up with the widest part of your shoe. If your heels are comfortable and secure and not tight. Then you may have comfortable shoes. That said, walk around and feel them. At the end of the day, you'll be less likely to want to wear shoes that don't feel good. No matter how good they look or how sweet their deal is. Fit is one of the most important elements of footwear. The costumes are much the same.
We're often asked "Which men's dress shoes are the most comfortable?" The answer is usually the same: what's best for you.
Note that none of these qualities require you to press the toe box of the shoe to test. Pressing down on the toe box when you're trying on shoes can be a fatal mistake. First, it just gives you bad information. If your toes don't touch the end of the shoe (you should be able to feel it through your toes), then the shoe is long enough. The distance between the toe and the end depends on the style. Whether a shoe is too long depends on the width and the feel of the heel.
Importantly, pressing your toes can damage your shoes! The shoe has stiffeners inserted into the toe box to ensure it maintains its shape. Depending on the brand, it can be hardened leather or plastic. Once the toe box is dented and deformed, there's nothing you can do to fix it. If you press too hard on the toe box, it may cause a permanent dent. Please do not press the toe box. It won't give you any useful information and may damage your shoes.
Now that you know a little more about how shoes should fit, let's talk about what styles are available and when you might want to wear them.




