When you are young, the thought of wearing dress shoes probably does not enter your mind too often, not at least in the sense that you will be actively doing so by your own choice. If you grew up religious or going to adults functions (both of which where your parents dressed you up), you probably were of the mindset that dress shoes were for special occasions. And a dress shoe in your mind was probably some very basic black slip-on loafer (think Ecco style etc). Because when we are young, chances are that we are running around, playing sports, being hyperactive, and of course, trying to look cool. It’s a shame, but dress shoes simply are not cool for young people, so wearing them when you are under 18 is generally seen as being snooty or something of that nature. It is not until we start to grow out of our adolescence that dress shoes start to make sense in our mind, and bear in mind that is still for the very minority of the population. Most people in this world, stay in casual sneaker-style shoes or more rugged wear (think Merrel/Ecco boots/Timberland etc) and really stay in that mentality that dress shoes are nothing more than shoes for special occasions and/or purely for work. Here’s is why that is not accurate.
Whether people care, realize it, find it offensive or whatever, the reality is and always will be that we are judged by our appearance. And the reason being is that our appearance nearly always says something about us as individuals and our personality on the whole. And of course, for me being ‘The Shoe Snob’ and all, that appearance always starts at the feet. And there are differences in how you are treated/perceived wearing one thing or another. I have been blessed enough to travel extensively in my life and with that is the awful experience of being inside of airports, my literal least favorite place. In fact, I cannot stand the airport and frankly a lot of the people that work there. And most likely everyone has had that bad experience in dealing with someone at the airport. They are not the friendliest of people and it is their job to automatically judge people by their appearance. And because I try to avoid losing my temper with airport people, I almost always dress up when traveling. And the reality is that when I do dress up, I almost never have any issues at all. But when I dress more relaxed and comfortable, it is not always the same. And while it is really silly as I am who I am no matter my clothing it is the reality of our world.
Our appearance is important, not only to give a good impression and not be judged by others, which is of less consequence but in reality, because if you have ever truly dressed nicely and been complimented on your style, I can tell you first hand that it feels damn good. And it is not really the acceptance and praise from others that feels good, but more so the internal feelings it gives you to be well dressed. It puts you into another frame of mind where the sky is the limit and you feel like you can be anything and anyone and achieve all that you put your mind towards. And it starts with a good pair of dress shoes because no matter how good your upper wear is, it all means nothing if your shoes are garbage. There is no fact in menswear that is more real than that. So, wearing dress shoes for appearance is not only a good way to look good for others and help them understand something about you, but more so for your own self progression in putting you in a mindset of achievement.
This will be an argument that I will go down swinging saying, but the reality is that comfort is not in how much cushion you have below your feet, but rather how well your feet are supported. I never understood that until my feet really started to hurt from wearing ill-fitting sneakers growing up and then ill-fitting blake-stitched shoes and finally into ‘proper shoes’ where my plantar fasciitis finally healed after wearing correctly fitting welted shoes. And I did not need some expensive orthotics to help. I just needed good shoes, with good arch support and in my correct size. A good pair of dress shoes, in reality, will fit you better and feel better than most generic ‘comfort’ shoes will. It may sound crazy but it is true. And the reason that it is true is that good dress shoes are built with good arch support in mind. Your run-of-the-mill Merrel’s or Ecco’s or Nike’s or any other casual shoe for that matter that is mass-produced out of China, India, Brazil, or the like, might feel good in ‘cushion’ but will not be providing you with proper arch support that your body actually needs for true comfort and posture. So, when you are thinking that dress shoes are uncomfortable because they have leather soles, guess what? You are wrong. I used to think that way too until I grew up and realized that comfort was not about cushion but rather about good support.
Find your support in a good pair of dress shoes!
The reality is that a good pair of loafers or chelsea boots or even a suede oxford can take you anywhere you want to go and in nearly any outfit. A smart loafer can be worn with any trouser the world has given us thus far. Maybe when we start wearing space clothes this point won’t be valid anymore but until then, it stands. And whether you are a snobby old-timer that only wears dress trousers or a young buck that only wears jeans, the fact of the matter is that there are many dress shoe models that can easily sit underneath both of those styles of dress and most other styles as well. But you cannot say that for any other type of shoe. Most suits cannot or should not be worn with shoes outside of a dress style, yet dress style shoes can be worn in more casual settings. Naturally, you would not go hiking in dress shoes but you would not in Nike’s either. Of course, there will be specialized shoes that always have their place, and naturally every now and then we just want to be relaxed in a pair of sneakers. All of things make sense and no one is saying that one should always wear dress shoes because they are the best. But, saying that, dress shoes, make you feel best (psychologically speaking), give you the comfort your body needs and can work well into most styles of dress, outside of a person who lives in the wilderness.
The reality is, the question is should not be ‘why wear dress shoes,’ but rather ‘why not wear dress shoes?’