How Should Dress Shoes Fit? – Men’s Clothing Fit Guide – Oxfords, Brogues, Derby, Loafers, Monkstrap

August 18, 2021 0 Comments

– Hi, I’m Ashley Weston. I’m a celebrity menswear stylist. If you don’t anything about me, click right here. This video is part of my men’s clothing fit guide. So I wanna talk to you about how your dress shoes should fit. I’ve seen so many articles and videos discussing all the different measurements you need to know regarding your feet like the length, the width, the arch, your toe-hair length.


Every little measurement that you need to know in order to find the proper fitting dress shoes. And here’s the thing. You don’t need to know any of that. I work with shoes every day, and all you need to know is your general shoe size. And that’s because every designer has a different definition of their sizing. So you can be an 11 in one brand, but a 10 in another. Just know your general shoe size, and from there, we’ll figure out and adjust to get the proper fitting dress shoes.

So there’s really only four things you need to know before trying on your dress shoes. First is knowing your shoe size. I’m assuming that you’ve worn shoes before and you should have a general ball park of what your shoe size is. And that’s what we’ll start with when you try on the shoes because, like I’ve said earlier, each designer, each brand makes their shoes differently.

The second point is your dress shoes should fit perfectly the first time. A big misconception is that your leather dress shoes will stretch over time. So if they feel a little tight, then why not just go get them. Leather over time it softens, it gets a little softer, so it’s not as stiff, but it only gives just a little bit. So you need to make sure that when you first try them on, that they fit already perfectly.

The third point is your feet swell throughout the day. So if you can, when you try on your dress shoes, make sure to try them on in the afternoon. That way you get a more realistic picture of how your shoes will fit. The last and final point that you need to know before you shop for your dress shoe is your feet are not the same size.

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There’s always gonna be one foot that is larger than the other. Make sure that your dress shoes fit the larger foot. It’s better that your shoes are slightly larger than slightly smaller. Now that we discussed the points you need to know before trying on your dress shoes, let’s go over the things you want to know and do when you’re trying on your shoes. Number one, the first thing that I cannot emphasize enough is try on your shoes with the socks that you would be wearing them with. So, I hope they’re not athletic socks, white athletic socks. And I hope they’re not also thick wool socks or thin socks. You wanna try on the shoes with the socks that you would normally wear. That’s key key key in order to make sure and get a realistic picture of how they’re gonna fit. The second point that you’ll want to know when you’re trying on your dress shoes is the length. So I have this Allen Edmonds Oxford dress shoe right here to help me demonstrate this point. So when you have your dress shoe on, you want to make sure that your feet so your toes, hit about right here. So you never want your toes to fill up this entire space.


So if that happens, if you feel any kind of pressure on your toes, like your toes are pushing up against something, then size up half a size, and if that still feels cramped, then size up half a size again. And that should definitely fix your problem. The next point is figuring out the right width of your shoe. Most men are, I’m gonna get a little technical here. They are a D-width. So that’s the width right here. They’re a D-width. You don’t really need to know this because most shoe brands don’t even specify this, and when they don’t, it’s usually because it’s just a D-width, it’s the average width that most men are. When you put on your shoe, you should not feel any pressure or scrunching around your feet. So nothing here, nothing anywhere.

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If you’re starting to feel pressure here, that means the shoes are not wide enough for you. So what I would do is size up half a size because you don’t wanna throw off the length of your shoe. See if that fixes the issue. If it doesn’t, then what you wanna do Is either try a different style in that brand or you’re just gonna have to try that sames style in other brands. But the beauty of dress shoes is, most designers all make similar styles. In the inverse, if the shoe, when you have it on, if your feet feel like they can literally slide left to right, if there’s a lot of room in there, then the shoes are too wide for you. So try sizing down half a size so that it’s more narrow, the width is more narrow. If that does not work, and there’s still plenty of room, then again, you’re gonna need to try another style in that brand or go with another brand.

One more thing on width. When they’re tied, if the two pieces right here touch each other, I know a lot of articles say that if they touch, that means the shoes are too wide. In my experience, sometimes some men just have not a lot of meat on the profile of their feet, the top of their feet, and so that’s why it’s touching. I don’t think that it’s an issue at all. As long as the width of here by the ball of your feet, right here, this is where it should fit as well as the length.

So if these two pieces are touching when you lace them, it’s not an issue. It doesn’t matter. The last and final point that I think is worth mentioning even though it should be a non-issue if you’ve gotten the length and the width of your dress shoes right is the heel of your dress shoes. When you have your shoes on, laced up, ready to go, start taking a walk. Take a couple stops, and your heel should not feel like it’s slipping out of your shoe. If it does, then it’s too long, there’s too much room.

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So then go down half a size, and that should fix the issue. Cheaply made dress shoes have this weird, stitching and layering on the back that can really rub at your heel. Do not get the shoes. You do not want to have to go through blisters and all of that uncomfortableness. It will not soften over time. It will never get better. Instead, save your time, your money, your sanity and go with another pair, another style, another brand of dress shoes.


You don’t ever wanna feel any uncomfortableness on the heel when you’re walking. All right, so that’s it. That’s all you need to know in order to find the perfect fitting dress shoes. I know a lot of guys out there are definitely hesitant about dress shoes because they feel like they’re uncomfortable and that’s not the case. You have to make sure the first time you try them on that they are comfortable, and if you hit these points, you will find the perfect fitting pair. Like I said in the beginning, this video is part of my men’s clothing fit guide.


Thanks so much for watching. Check out my website for more in depth article that goes over all of these points in more details, and I also include my favorite dress shoes that every man should own. Subscribe to my YouTube channel for more videos like this, and if you like this one, give it a thumbs up. All right guys, I’ll see you in the next one. (majestic music)