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Butterfly loafers by J.FitzPatrick Footwear


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.

I love being casual, like on the right side, but for sure am regarded as more ‘respectable’ when dressed how I am on the left. In fact that very day, I was treated as ‘the breadwinner’ because I was dressed like that while others were more casual and was handed the bill at the restaurant with a table of 5. Go figure!



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.

My good friend Martel Francois, looking smart in both outfits but definitely next level in that suit and brown suede monks!




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!

Norman Vilalta shoes, look at that arch shape, cupping the arch region. True comfort there!
Simon Crompton in bespoke dress shoes, the ultimate in comfort



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?’


Hugo Jacomet in his TLB shoes. A pair of bi-material brogues like this are so easily transitional from casual to dress attire all in a day’s flash!
Me, all dressed up in a suit by Jake Mueser and some simply black penny loafers that are easily worn across all styles of clothing

15 thoughts on “Why Wear Dress Shoes?”

  1. I do agree! Not enough people don’t wear dressy shoes. Shoes that are versatile enough can be worn for both work and play (cap toe boots and loafers, depending on the office). Casual shoes are just that: casual. Some try to wear them with suits, but that’s just weird especially when its the flashy ones like Air Jordans.

    I do agree with the point where people think more cushion = better comfort. I’ve only started enjoying true comfort when I started wearing GYW shoes. Even my Allen Edmonds are way more comfy than running shoes and sneakers if I have to move about. I only wear running shoes when I’m in the gym. Else they just throw the entire outfit off.

    A point that I get from people is that “dress shoes are expensive”. But then, many don’t think that the value of a pair (or several) will be cheaper when taking into account the durability, longevity, reparability and comfort of a good pair of shoes. Why pay $250-300 for a pair with custom orthotics that have 2 inches of foam and look ugly as hell, when at that price one can get a decent, good looking pair of dress shoes?

    Thanks for writing this article. Cheers!

    1. Justin FitzPatrick

      Thank you for sharing Yap! And yes, I did not touch on the price part and the simple fact that some people want dress shoes but cannot afford them but this was more about those that can afford them but choose to wear other stuff

  2. Great post Justin. I grew up with sneakers and boat shoes. Now I am fortunate to wear some of the best shoes that I bought at my time with Bergdorf Goodman. My collection goes from Magnanni to John Lobb. All with character and great support. I hope this post changes more men’s thoughts about dress shoes.

    1. Very well-said, Justin. And I also agree with Yap and Pierre. I would add one thought. I spent my life being very particular about my dress clothes. I progressed from Brooks Brothers to Zegna, Canali to Brioni to bespoke. But I’d top of my wardrobe with a pair of JM (before they sold) or AE’s. And over the years my body changed. For about 30 years it was constant alterations and growing from a size 40 to my present 44. It happens to most of us. But guess what? The shoes still fit! So one added advantage of dress shoes is that they will fit you forever. Since I discovered high-end shoes I have been upgrading my collection without regard to price. Last week my first pair of Conblers Union and my second Paolo Scafora’s arrived. They will last me forever and my collection will be handed down to a grandson who is my size. I only wish I had known about good shoes when I was 30. I’d be miles ahead. So, when considering a pair of $500, $1,000, $1,500 shoes or more, remember that over time, if you are careful about fit, don’t hesitate to pull the trigger. They are the most sound sartorial investment you can make!

      1. Justin FitzPatrick

        Thank you for sharing Peter, I do appreciate your constant support, not only in the blog but also in the brand.

    2. Justin FitzPatrick

      Thank you for sharing Pierre and for all of your support! Hope to see you soon in the shop when you happen to be around Soho.

  3. Thanks for sharing your thoughts on this, Justin.

    Like your table of 5 and airports exemples, I’ve personally seen how people look at me differently since I wear dress shoes, and even dress up more. Even despite often being the youngest in the room…

    Tempted to say… Footwear maketh man!

  4. Justin
    thank you very much for writing this article. I hope I could read this kind of article 20 to 30 years ago.

    Anyway, it is better to be late than never. I started few years to learn about dress shoes and start to build a small and compact collections with careful thoughts and planning of their applications on occasions.

    thank you once again of your wonderful contributions to the large audience like us through the shoe snob.

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