Men's Clothing Fit Guide

How Should Dress Shoes Fit?

This article is part of my Men’s Clothing Fit Guide.

I’ve seen so many articles and videos taking how to get the proper dress shoe fit that are completely unnecessary and just create more useless work and steps for the poor readers. Of course, if you ask a shoemaker or shoe salesperson about what goes into fitting for a pair of dress shoes, they’ll tell you about the painstaking process you must endure as they pull out their Brannock device and start measuring the length of every toe hair in relation to the current barometric pressure. As someone who dresses and fits men for shoes as part of my career, it’s all hogwash.

Never once, in all my years, with all my clients, have I ever needed to get an exact measurement of their feet – and this is because the brands and manufacturers don’t work this way. Their sizes aren’t universal and can vary wildly between brands. So a 9 in one brand might fit the same as a 10.5 in another brand. Each one is different, so it’s great that you know your right foot is 10.236 inches long by 4.789 inches wide, but that really doesn’t matter unless you’re getting custom made shoes.

So what you have to do is try on dress shoes and figure out how to get the best fit in that style/brand. Let me show you how.

Before Trying On Dress Shoes

You should know and do these few things before trying on dress shoes.

1. Know Your General Shoe Size

I’m assuming you’ve worn shoes before and have a general idea of your size? Great! That’s all you need. Like I said earlier, since each manufacturer has different fits and sizing for their shoes, it’ll all be trial and error anyways. The thing you want to do is get in the ballpark and use that as a starting point.

2. Dress shoes should fit perfectly the first time you try them on

If they don’t, they’ll never fit. Leather, especially in dress shoes, will stretch very, very little, so “working in” a pair of dress shoes is not going to happen and will be a waste of your time and money. One of the worst things ever is wearing a pair of uncomfortable shoes – as a woman, I know this all too well!

3. Your feet swell throughout the course of the day

So, if you can, try on shoes in the afternoon. This way, you’ll get the most realistic size and fit of the shoes.

4. Your feet are not the same size

Make sure the shoes fit your larger foot first, not the smaller one. Slightly too big is not uncomfortable, slightly too small is very uncomfortable.

How To Try on Shoes

When you’re trying on shoes, here’s the things to do and look out for.

Socks

Wear the type of socks that you will normally wear with these shoes. In other words, don’t wear your thick woolen socks, or your super thin ankle socks when trying on dress shoes.

Length

If you feel ANY bunching in the toes or feel the shoe pressing against any of your toenails, they’re too short. I see some places talking about your toes grazing the front of dress shoes – this is not correct.

Your feet shouldn’t be touching or grazing anything in the front. If they’re grazing, that means when you walk, your toes will be jammed into the front of the shoe, because your feet will shift slightly forward as you walk, which is very uncomfortable. Either go up a half size and if that doesn’t fix the problem, it might be a style or width issue. So try a different style or a different brand that makes the same style. Luckily, with dress shoes, they’re pretty darn similar, so you’ll find an equally great one, I promise.

Width

The shoe should not be putting any pressure or squeezing on the sides of your foot – anywhere. If you feel anything like that, you may need to go up half a size and see if that fixes the issue. If it doesn’t, you can see if they make a wider size in the same style. If they don’t, then try a different style or brand. Some brands are wider than others.

On the flip side side of that, you also shouldn’t have any room on either side of your foot that allows your foot to move left or right when it’s laced up. If this happens, go down half a size and see if that fixes the issue. If not, you can ask if they have a narrower width in this shoe. If not, you may need to try a different style or brand.

The average man has a medium width of D. If a brand doesn’t specify a width, which most of them don’t, this is probably the width they use. Again, though, a brand’s definition of a D width varies, so watch out for the differences. A narrow width is a B, a wide width is E and an x-wide width is 3E.

If your foot falls between a B and a D, go with the larger width.

I see some places saying that if they’re lace-up shoes, like an Oxford Dress Shoe (Which they almost always should be, if they’re dress shoes!), you should not be able to tie the laces so tightly that the two edges of the shoe meet. I don’t adhere to this advice because some of my clients just have less meat than others on the tops/profile of their feet and when this happens, it’s not a problem. As long as the shoe fits everywhere else, I wouldn’t about this part.

Heel

If you have the width and length in check, this shouldn’t be an issue, but just in case: You want a little bit of space between your heel and the shoe, but not too much. My one finger test for sneakers is not applicable here. They should fit a little snugger than tennis shoes do in the heel, but should not be pressing against your heel as to be uncomfortable.

Lace up both shoes and take a short walk in them. There should be little to no slippage in the heel. If there is, they’ll create blisters on your heel and that’s not fun.

Also, since I hear this complaint a lot from guys – If there’s anything like a seam or stitching rubbing against your heel, don’t get those shoes. This is mostly typical in cheaper shoes. This area will never “break in”, so if something is rubbing against your heel when trying them on, it’ll never go away, so stay far away from them unless you like blisters on your heels!

The Best Dress Shoes For Men

See my Men’s Wardrobe Essentials – The Oxford Dress Shoe for my picks.

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