How Should Dress Shoes Fit? The 2024 Sizing Guide!

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Your shoes are the cornerstone of your outfit. Having a great-fitting pair of dress shoes powerfully increases your style game.

Poor-fitting dress shoes are not just uncomfortable but can also wreak havoc on your feet, leading to issues like painful blisters.

Despite their appearance, like any clothing item, the importance of a proper fit cannot be overstated.

Now, let’s delve into the key question: How should your dress shoes fit? And are you wearing the right size dress shoes for your feet?

How Should Dress Shoes Fit?

Let’s start by debunking a common myth that says that dress shoes are inherently uncomfortable.

More often than not, the discomfort that you experience is because you’re using the shoe for something that is not intended for.

You wear a pair of Allen Edmonds Fifth Avenues without breaking them in first, wear them too tightly, or subject them to extensive walking of 10 miles a day. Naturally, it’s going to be killing your feet.

Such discomfort can be attributed to improper sizing and the way your foot fits inside the shoe, which results in hot spots and numbness due to tightness.

Conversely, loose-fitting shoes allow the foot to move excessively, which can cause blisters.

Now that that myth is out of the way, let’s discuss the essential steps to finding a perfectly fitting pair of dress shoes.

How Dress Shoes Should Fit

First and foremost, always use a shoe horn when putting on dress shoes to prevent potential damage to the back heel over time.

Now, let’s focus on the critical areas to consider when trying on a new pair of shoes.

The ball of your foot should sit comfortably in the widest part of the shoe, known as the shoebox. It should grip closely around your foot without being overly tight; aim for a Goldilocks fit—just right.

Forget about the old rule of pushing to see where your toe ends inside the shoe; what truly matters is the fit within the shoebox.

You want to have ample room for your toes; they shouldn’t feel cramped. Keep in mind that different shoe styles have varying shapes; some are designed to be longer and some have a pointed end. The key is to ensure your toes don’t touch the front of the shoe, regardless of its shape and you’ll be fine.

Next, check the fit around the heel of the shoe. It shouldn’t slip as you walk. If you notice excessive movement up and down at the back of the shoe, you’ll need a smaller size or to go with a different brand.

Now, I need to point out that this rule primarily applies to laced shoes and boots. For slip-on styles like Chelsea boots or loafers, a bit of extra room in the heel area is acceptable.

It’s also very important to walk around to assess the fit of the shoes. Simply sitting or standing in them won’t provide an accurate feel for how they fit during regular use.

Lastly, pay attention to any discomfort or chafing when you walk. That typically indicates a shoe that is either too small in length or width, or conversely, too large if your feet are sliding around inside.

Use A Brannock Device

Don’t expect to find a perfectly fitting and comfortable pair of dress shoes within the first few minutes of stepping into any store.

Take your time to explore different styles and find one that fits your foot well without causing discomfort.

A Brannock device is a helpful tool that measures the length of your foot from heel to toe, the length of your arch, and the width of your foot.

It can determine if you have a wide or narrow foot as well as identify whether one of your feet is longer or shorter than the other.

Place your heel against the back of the Brannock device and look directly down over your longest toe to see the measurement. This number marks the total length of your foot.

Then, slide the pointer to the ball joint of your foot. This number will give you your arch measurement.

Now that you have these two measurements, compare them. Whichever number is bigger will be your shoe size.

To measure your foot width, adjust the width bar of the Brannock device to the side of your foot and make note of the corresponding letters: A, B, and C indicate narrow widths, D is average, and E, EE, and EEE are considered wide.

Now that you have your foot measurements, you now have a solid starting point.

However, it’s important to recognize that sizing and widths can differ significantly across brands. The reason is because each brand has their own shoe last. A shoe last is a wooden mold which the shoe is formed around.

Now, because each brand has their unique shape, and their unique lasts, you’re going to find that there is variation across the brands.

For example, my feet are slightly wider, ranging between sizes D and E. However, my right foot measures 11.5, while my left foot measures a size 12.

A lot of boots have a higher volume so you can get away with sizing down more and still have a lot of room for your toes. On the other hand, dress shoes tend to be narrower.

Like I said, I had to go up one width just to get that right size in the middle of everything and just have it be a happy medium.

Wear Dress Socks

When it comes to socks, dress socks are thinner compared to thicker cotton athletic socks. They’re also going to come up higher and if you get what’s called over-the-calf dress socks, they’re usually going to be able to come almost all the way up to your knees.

That way your socks aren’t going to be coming down constantly throughout the day.

Fans of quality socks often praise Bombas socks for their remarkable ability to stay up consistently. You can choose the version that aligns better with your style and preferences.

Next, you need to understand that your size isn’t always your size…

Your Size May Vary From Brand to Brand

Take a moment to examine the footwear you currently have. You’ll likely notice a slight variation between your boots, casual shoes, casual sneakers, sporty sneakers, and running sneakers.

For example, I wear a size 13 in athletic shoes. Yet, when it comes to my Vans Old Skools or canvas slip-ons, a size 12 fits me perfectly every time. I wear a size 11 in both Clarks Desert Boots and Red Wing Iron Rangers, while for Allen Edmonds 65 Last, I wear a size 11.5E. I chose a wider width in the Allen Edmonds shoes to ensure the comfort level I prefer.

Your Feet Swell Throughout the Day

Keep in mind that your foot size can vary by up to a quarter of a size at different times during the day. For instance, you might measure as an 11.5 regular D width in the morning, but as the day progresses, your foot may expand, leading to a measurement closer to a 12 wide or 11.5 wide due to swelling.

Not only that, factors such as hydration levels and sodium intake can also influence foot size. These variables play a significant role in determining how well your shoes fit throughout the day.

It’s a good idea to try on your new shoes later in the afternoon or evening when your feet tend to be slightly more swollen from daily activities. This way, you can find a fit that remains comfortable throughout the day.

For example, when I wear my Fifth Avenue shoes in the morning, they often feel loose. However, as the day progresses, they conform better to my feet to a point where I start to feel a slight pinching on the sides of my forefoot, but it’s a happy medium.

If I went any bigger, it would have been too loose and if I went any smaller, it would have been too tight.

If you already have some shoes that are too tight, you can always try to stretch them using some of these stretching tecniques.

Try On Your Shoes In Store

The most critical step in determining if a shoe fits properly is when you try it on. While this may seem Captain Obvious, but understanding what to look for during the fitting process is key.

I’ve made all the common mistakes: I bought shoes that are too long, too wide, too narrow, or even too short. However, these experiences have taught me valuable lessons.

Now, I have a clear understanding of how my dress shoes should fit. I prioritize comfort, ensuring that they won’t cause any unnecessary discomfort during long hours of wear.

If you have an Allen Edmonds or a DSW-type store conveniently located near your workplace, consider trying on shoes during your lunch break or on your way home.

Alternatively, you can order three pairs from Zappos. If you typically wear a size 11.5, start with sizes 11, 11.5, and 12. Test the shoes in different conditions: in the evening, during hot weather, in cold weather, and even after drinking plenty of water.

That is how I’ve done it and that is how you can do it, too. Now, all the dress shoes I’ve purchased have fit perfectly and have never felt too narrow, too long, or too small.

Hopefully, you don’t make this mistake because it cost me quite a bit of money to make this mistake.

Same Lasts Will Fit Very Similar

Some shoes are crafted on the same last, while others use different lasts, which serves as a helpful starting point in understanding their fit.

To clarify, a last refers to the shape of the shoe. For example, the McAllister, Fifth Avenue, and Park Avenue are all built on the 5 last. Therefore, an 11.5E in a McAllister will also be 11.5E in the Fifth Avenue.

When trying on both the McAllister and the Fifth Avenue, I’ve noticed that the McAllister fits a bit snugger than the Fifth Avenue. While the overall fit is similar, the McAllister feels sturdier, whereas the Fifth Avenue feels more flexible.

Because there’s a little bit more leather, the Mcallister just does feel like it’s a little bit more resistant. Initially, it may feel a bit loose in the morning, but as the day progresses, it may tighten up a bit more compared to the Fifth Avenue.

However, as long as I don’t experience heel slippage, I prefer this snugness because opting for the 11.5D (standard width) would cause discomfort along the sides, so I prioritize a snug yet comfortable fit.

All right, guys, here are a few pro tips.

Pro Tips

Buying Dress Shoes for the First Time

If this is your absolute first time shopping for a pair of dress shoes, I suggest starting at retailers like DSW or exploring options on Zappos.com for a hassle-free experience.

DSW offers a wide range of options, making it easy to explore different styles. Personally, I often purchase sneakers and some boots from Zappos.com due to their convenient return policy.

You can buy multiple pairs to try on, and returning them is as simple, much like handling an Amazon return at a nearby UPS store.

While DSW may not have a vast selection as some specialty stores, it’s a great place to begin your search and get a feel for different styles. This is how I discovered some newer brands in my own shoe-shopping journey.

Try On Carpet

When trying on leather sole dress shoes, only walk on carpeted areas. Avoid walking on hardwood or concrete floors, as this can scuff the bottom of the leather soles, making them non-returnable.

Consider The Bigger Foot

It’s common for one foot to be slightly larger than the other. In such cases, make sure to size the bigger foot to accommodate it comfortably.

Be Prepared To Make Mistakes

Be prepared for some trial and error when buying certain dress shoes and experimenting with different sizes. Even after following the advice I’ve shared, it’s still possible to end up with the wrong size and not realize it until it’s too late.

Changes in your daily routine can catch you off guard. You might transition from a desk job where you walk minimally to a more active role where you’re on your feet frequently, such as meeting clients and covering long distances, can expose the limitations of your current shoes, which can be frustrating if you hadn’t anticipated it.

In such cases, you may need to go bite the bullet and get another pair of shoes, which can be always annoying. It’s essential to budget for these potential mistakes and aim to minimize them as much as possible.

Start With Less Expensive Dress Shoes

If you’re not sure, it’s wise to be conservative with your budget. Don’t rush to pay full price for a pair of dress shoes that you’ve never worn before. There’s a high chance that you won’t achieve optimal comfort out of your shoes and you’re going to be looking to replace them sooner than anticipated.

Now that you understand how to properly fit your dress shoes, you have no excuses for wearing the wrong size shoes.

Thanks for making ti to teh end of this article and I’ll see you in the next one.

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