top of page

5 Tips on Dress Shoes: Do's and Don'ts

Updated: Jan 13, 2019

Decisions decisions. Purchasing a pair of leather dress shoes is never an easy task. From whether 'I would be able to match them with my outfits' to 'how long will this pair of leather shoes last', there are just many things that we need to think thoroughly before making the decision to buy a pair of dress shoes.

Back in the days when I was first exposed to classic menswear, I made a lot of wrong purchasing decisions that I still regret today. Thus, in this article I will be sharing with you all 5 tips on dress shoes -- what you should do and what you shouldn't. Hopefully after reading this article, you won't repeat the same mistake that I made.

Chestnut Brown Oxfords from Cheaney's

(1) Keep it simple at the beginning

Admit it, when we first get the opportunity to choose our very first pair of leather shoes, we all have that moment that we want to get something truly one-of-a-kind. However, this often means the pair of shoes are not versatile at all. What ended up happening is either we wear this pair of shoes only once or twice a month or we run into the problem that everyone would immediately recognize that pair of shoes if you wear it more than once a week.

Now you may recall that in my Guide to Monk Straps, I said that what leather shoes to get truly depends on the individual. As much as I would encourage you to get a pair of dress shoes that is distinctive, your very first pair or first pairs of leather shoes should either stick to the basics or be coherent to your daily lifestyle.

Thusly, when you first build your collection of leather shoes, you can a pair of classic brown oxford shoes as shown above; or if you are in a situation like mine, you could start with a pair of brown monk straps. But in any case, a pair blue alligator derbies as a start-up is definitely a no.

(2) Stay away from Square-Toed Shoes

Have you ever seen one of those ugly square-toed shoes on the streets? Chunky and unrefined, it is like if the designers are trying their best to remove the elegance from a pair of leather shoes.

One of the biggest mistakes that I have ever made was to purchase the black patent leather derbies as demonstrated above. Even though they are not as notorious as the boxy, squared-toed loafers that you would immediately throw up whenever you see them; they are impractical, poorly-made. Definitely something that you would want to avoid.

Dark Brown Alex (whole-cut oxfords) from Crockett and Jones

However, it is a different case for the English chiseled toed shoes. Even though they are squared-toed, you could see they are tapered from the widest point to the toe. They are extremely elegant; and often you can tell they are high-grade leather shoes.

Thus, my best advice to tell the differences between squared-toed and chiseled toed is that if the shoe doesn't taper much from the widest point to the end of the toe, then it's indefensibly square-toed.

A pair of high quality leather shoes as exemplified by its two-tone toe cap.

(3) Quality over quantity

As cliché as this may sound, this golden rule is applicable to all sorts of clothing-purchases, and particularly for dress shoes. Throughout my early years, I purchased quite a sum of leather shoes that were rather low in quality. It is often the case that I had to throw away these shoes after one or two years either because of their unendurable leather or their fragile rubber soles.

Now you may argue that they are more affordable than higher-grade leather shoes. As much as these leather shoes may be cheap at the first glance, they actually have a higher 'cost per wear.' In contrast to low-quality leather shoes, even though they are more expensive at first; because of the fact that they are more durable and the fact that you could take them for repairing, the money you spent on that pair of leather shoes is actually less than you would otherwise spent on several pair of dress shoes.

Stitchings could often be found on the sole of a goodyear-welted leather shoes.

In other words, my advice for you is to save up for a pair of good-quality shoes rather than buying many pairs. You should buy timeless designs that could be resoled so that even when the sole of the dress shoes is worn off, you could just take it to a cobbler to have them fixed.

Usually, a good indication for a pair of higher grade leather shoes is that they are goodyear-welted or even hand-stitched. What that means is that rather having the sole sticked or stitched directly to the leather, it is stitched to an extra layer that is underneath the leather. Under such circumstances, you could technically wear this pair of leather shoes forever as long as you take good care of it.

(4) Sale shoes are not always a good deal

Even though I would agree that sale could sometimes be a great time for you to look for discounted clothing, it is not always the case. For me personally, while I was able to buy a pair of goodyear-welted leather shoes for just £150 that would otherwise cost £350 usually; I also happened to buy the black patent leather derbies as shown above during a sale event. In other words, I am rather mixed towards shoe sale events.

In order to determine whether the pair of sale shoes is the right choice for you, there are several factors that you need to look into. Firstly, the pair of leather shoes should fit comfortably. Secondly, check if it is a pair of goodyear-welted leather shoes that could be taken for resoling. Thirdly, whether they are particularly markings or damaging that made this pair of leather shoes being placed on sale. You should definitely avoid those that have some serious markings as this would just be a waste of money.

(5) Use shoe trees and polish your shoes regularly

Lastly, make sure you try your best to keep your leather shoes in good shape. Getting a pair of high-grade leather shoes yet not taking care of them is a sin in my own opinion.

In order to keep your leather shoes neat all the time, you should polish them once in a while and put shoe trees in whenever you take them off when you got home. Getting a pair of shoe trees that have a similar last to the leather shoes could keep them in shape and take away the moisture your feet give off throughout the day. If you think getting a shoe trees for every pair of dress shoes you own is too expensive, it is totally fine to have a shoe tree shared among several of your dress shoes.

Ending with an interesting note, the level of polish is something that you should bear in mind as well; but I shall discuss this in a greater depth on another day.



bottom of page