Dress Shoe Buying Guide (10 Mistakes to Avoid)

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Dress Shoe Buying Guide

Shoes are the foundation of your wardrobe, they’re worth investing in.

That being said, nobody wants to waste their money on a pair of dress shoes that they never use.

In this dress shoe buying guide, I’ll talk about ten mistakes that you want to avoid when you’re going out there and investing in high quality shoes.

Equating Value With Price

Mistake number one and the biggest mistake that people make when they’re buying dress shoes is that they equate value with price. They are not the same thing.

Let me introduce you to my style theory of value.

The style theory of value goes that value is equal to the number of wears times the way it makes you feel divided by the price.

So, you bought the shoes for 50 bucks, you thought you were getting a great deal, but when it comes down to it, you put them on, they hurt your feet. And you wear them a total of five times.

How did they make you feel on a scale of 1 to 100? I’ll be generous, I’ll give them a 10.

So, we’ve got 5 times 10 = 50. 50 divided by 50, a value of 1.

Other pair of shoes cost you $500, but when you bought them you just love the way they look, the way they fit, the way that they feel.

You wear them five hundred times over the next few years and how do they make you feel?

On a scale of 1 to 100, they make you feel like a million bucks.

A hundred we’re going to give it. So, 500 times 100 divided by 500. This have a value of 100.

I want to stress, I’m not saying that you got to spend $500 on a pair of dress shoes, what I am saying is pay attention to how the shoes fit, pay attention to how they make you feel and those are the key factors.

When you get a pair of shoes that you absolutely love, you find excuses to wear them and they make you feel like a million bucks and that’s what style is all about, building up your confidence, so you can go out there and be the man you know yourself to be.


The next mistake you want to be careful of when investing in a high quality pair of dress shoes is overpaying.

There are two main ways you’re going to be overpaying.

One is you’re going to go for a fashion label, you’re going to go for a brand name, but oftentimes you’re just paying extra.

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A lot of margin to that brand, simply to get that name and no one’s going to be able to tell on the shoes.

Another way you could overpay is you can go with a particular brand that really is a great brand, like John Lobb or maybe Alden. But, the problem is not everyone needs to be spending $800 or over $1000 on a pair of shoes.

I personally believe that there are so many options out there. With the internet, it has really leveled the playing field.

Nowadays, you can buy directly from companies that don’t have big store fronts and are able to pass on the savings.

Going With Eccentric Style

The next mistake you want to avoid when buying quality footwear is don’t start off with an eccentric style. You want to go with a classic workhorse.


Because you’re going to get more wears out of it.

For example, a black, cap toe oxford shoes are going to work with any type of business attire, a suit.

Maybe you want something a bit more casual, then maybe you go for a blutcher in brown, a little bit of a cap toe.

If you buy something that’s eccentric, I’m not saying that you’re not going to wear it, and maybe it could be a great investment.

But, I do think that you should start with your foundations first.

Not Spotting Quality

The next mistake men make when they’re investing in high quality dress shoes is they can’t spot quality.

They think they got a great deal until they notice those shoes are glued. These shoes are made out of plastic. Just because it’s shiny does not mean it’s stylish.

The issue with poor quality shoes is not so much the gluing, I mean that’s bad because it’s eventually going to fall apart and it can’t be resoled.

But, really if they glued the shoes together they didn’t use quality components on the sole, they didn’t use quality components on the upper.

When you’re looking at a pair of shoes, you want to make sure what type of construction did they use. You want to look for a Blake stitch or you want to look for a welt stitch.

Both of those are great and some people prefer one or the other.

But, what you want to look at is the stitching and on the bottom not always going to be possible. It might have a rubber sole and that does not mean that it isn’t going to be blake-stitched or welt-stitched.

But, what you normally want to look for is going to be a leather sole and you can see the stitching. With the welt stitch, you are also going to be able to see stitching on the outside.

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With the blake stitch you won’t be able to see that, you would actually have to take out the inner lining of the shoe and you would see the stitching on in there.

Not Paying Attention to Details

The next mistake that men make when they’re buying high quality dress shoes is they don’t pay attention to the details because they don’t know what details to look for.

First off, look at the heel of the high quality dress shoe. It should be something that it’s broken up into multiple pieces. Layers of leather.

These layers of leather do have a bit of glue in there, but they should have tacks. Basically, small nails that are right in there. This is a sign of high quality.

Another small thing I like is when they’ve got a bit of rubber, it gives you a little bit of traction. Each company does this a little bit differently.

Another thing, when you see broguing on a shoe, and those are small leather holes perforations, you want to make sure that they’re very clean.

Another thing you want to look at when you’re going in and you’re looking on the inside of the shoe is that it has a leather lining.

If it doesn’t have a lining, then basically there’s not protection from your sweaty foot to go to the outer part of the shoe.

Another thing is the stitching. If they’ve got that lining, you want to pay attention to the stitching. They should be a single stitch and it should be pretty even around the edges.

Men's Dress Shoe Buying Guide

Buying Only One Pair

The next mistake is only buying one pair. I’m not saying that you got to get the same exact pair.

But, you know what?

If you like that little bit of contrast, why not get two pairs of shoes that serve.

The thing is you don’t want to have one pair of high quality shoes that you wear every single day. You want to rotate. You want to give the shoes time to breathe.

No Matching Belt

Another mistake, you want to make sure before you leave the store that you find a belt that matches. Most companies are going to have a series of belts that work.

Another thing is to find a polish. Ask them which polish you can apply.

But, in any case no matter what they tell you, make sure to always test the polish on the tongue of the shoe and see if it does any type of discoloration before you actually apply it on the upper.

Not Using Shoe Tree

And, speaking of breathing, the next mistake is not taking care of your investment. You want to have a quality shoetree.

A shoetree made from cedar is going to pull a little bit of moisture out, but also it’s going to keep the shape of the shoe.

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So, you want to invest in a quality pair of shoe trees specifically those made for the shoe.

Not Using a Shoe Polish or Conditioner

The next mistake, some guys think that polishing their shoes or using a conditioner is optional when it comes to your shoes.

Guys, if you want your shoes to last, especially more than one winter, you need to take care of them.

This is your first line of defense.

What this does is when you put a wax on them, it creates a thin film of layer. That layer will protect your shoes not only from the elements, from water and from salt, but also abrasions.

So, whenever you knock it up against something, guess what? It just knocks the layer of wax off, it doesn’t penetrate the shoe. Sometimes it will, but what you’re looking to do is create that thin layer of defense that’s going to help your shoes last longer.

Not Storing Shoes Properly

The next mistake men make after they’ve invested in a high quality pair of dress shoes is they do not store them properly.

Whenever your shoes are a little bit moist, do not put them next to heat, next to heater, next to a fire, that is going to damage the leather on your shoes.

You want to make sure to use that shoe bag. If you bought form a high quality manufacturer, they should have given you a shoe bag.

Also, keep the shoe box because you can put them in the shoe box and that actually allows you to stack them in your closet.

Bonus Tip

Do not work with companies that don’t care about you.

Basically, companies that have bad customer service and they’re out there. I hate to say it, but there are some companies that honestly don’t care.

I like smaller companies or larger companies that have great customer service because for me, if I’m going to spend good money on a pair of dress shoes, I want it to be something that’s going to last a long time.

And if the stitching starts to come apart, which can happen on any company, with any type of build, you want to make sure that you’re going to be taken care of.

buying dress shoes

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