As a heads up to those that don’t know what to look for when getting a pair of dress shoes I thought that I would put a list together of what DEFINITELY not to do, but also paired with options that would be more favorable. There are certain rules to adhere to, in order to maintain a healthy and respectable look, when it comes to purchasing dress shoes especially when considering all of the factors that play into it. Here are my five rules of what to do and what not to:

1. Leather Quality

What Not To Do: Never, ever buy that high-gloss leather that looks like patent but is not. You will know the one that I am referring to if you touch it and it feels like plastic and usually it is pretty close to being that. You see Kenneth Cole and brands of that price point using this type of material and it is crap. It wrinkles very easily and stays that way forever and also cracks very easily due to it’s lack of quality and the fact that it is super rigid. Another thing to look out for are leathers that smell like chemicals. The only things a leather should smell like are it’s own aromas or the polish that the people at the factory gave it before it was shipped to the distributor.

What To Do: First thing is: always ask if you are not sure of anything! But what you should look for in a superb leather is something that is supple yet firm. A French calfskin is usually the most popular with the upper end shoe brands and is so because of its durability but also of it’s quality to feel like silk on your feet after broken in. Stiffer leathers like cordovan and that of Church’s leather also tend to be of higher quality but will definitely be much harder to break in but once they are you can believe that you will have a shoe that you feel completely supported in.

What To Know: Leathers are not indestructible!! They will crease and will crack if you do not treat them properly. NO LEATHER IS WRINKLE FREE!!! IS YOUR SKIN???? NO!!!! Use shoetrees and get regular shines or polish them yourself once every other week.

2. Heels

What Not To Do:Unless you are below 5 feet tall you should not be wearing heels that are much higher than 3cm or 1.2in. You will look like you are wearing boots and it just doesn’t correlate with the look of dress shoes, it just throws them way off. If you are unsure of how to tell take a measuring tape with you but in all honesty, it’s not hard to see the difference and below I will post two pictures of what is right and what is wrong.

too high by Saion
just right heel height by Anthony Delos

While the shoe on the top is still a beautiful shoe is just looks funny to me and would look even funnier on someone who was wearing them with a suit. While it’s only a slight difference in terms of measurement, it’s difference on the eye is immense.

3. Toe Shapes

What Not To Do: Anything too extreme is just not attractive by any means. A shoe should never be too square, too pointy or too round. It just doesn’t look good and I know I have said this before and believe me I will say it again because it just doesn’t seem to get through. Leave the corner kickers to the elves, the guillotine-toed shoes to the douche bags and the shoes that have a toe that looks like a perfect semi-circle to the old people with pancake feet. (Refer to Our Toe Choices-What A Shame)

What To Do: Avoid anything super symmetrical and choose something that has elegant curves that compliment each other to create a shoe that resembles the silhouette of your foot. However, since some of our feet are a little blunt looking, a little elongation in your shoe’s toe box never hurts as long as it is not too extreme. (Perfect example below by Gaziano & Girling)

4. Silhouettes

What Not To Do: Pair shoes and suits that do not compliment each other. What I mean by that is: don’t buy shoes that are slim looking but you tend to wear suits that are a little more baggy looking i.e. not slim fit. And vice versa, do not buy thick ass shoes with bulky ass soles if you are someone who always wears skinny suits. I know this was a Thom Browne look but to me it is just silly looking, you might as well buy a Neil Barrett suit and strap some bricks on your feet if you like this look but to me it is just too disproportionate and is not eye catching nor elegant. But please, more than that, DO NOT wear baggy suits with sleek shoes, it just looks terrible and better yet just don’t buy baggy suits, wearing baggy things should have ended for you at 20. Not saying wear things that are only slim looking but wear things that actually fit the silhouette of your body and feet and keep them correlating with each other; slim suits with slim silhouette shoes and more gracious suits with heavier looking shoes.

What To Do: Get a second opinion from a trusted expert if you can’t fathom what I am telling you! Here is an image of a good makeover, take notes!

5. Take Good Advice

What Not To Do: If you are out of college and at the point where you need to start making decisions for yourself then what you should definitely not do when looking for dress shoes is ask your father what he thinks, especially if he is wearing baggy suits, old man loafers and is the type that has worn the dark suit with black shoes for 30 years! The only exceptions to getting his advice if he has a tailor (or at least has his suits altered more than at the sleeve and cuff when buying suits), wears brown shoes with suits and thus plays the part of a smartly dressed individual. Other than that, take his money but leave him at home!! While I am sure that there are many stylish fathers out there, my issue is in having seen far too many times young men shop with their fathers and the father is trying to turn his son into a mirrored version of himself (when the father is not stylish). It’s sad and we will never grow more stylish as men if we are just emulating our father’s dated style sense, especially when it comes to the more conservative old man that still believes “no brown in town.”

What To Do: Find the most stylish looking person in the store and ask their advice!!!

41 thoughts on “5 Rules For Buying Men’s Dress Shoes”

  1. R. Gratz, thanks for all of the compliments, please do pass it on, i would love to spread the good word. Thanks to everyone else for the other compliments, glad to post enjoyable knowledge.

  2. Dear Alan – I tend to generalize sometimes, it makes for a stronger affect on my opinions. I know that there are many men over fifty who dress very well. I am glad that I have been able to help and that you seem to enjoy the blog. Thanks for commenting. All the best,-Justin, "The Shoe Snob"

  3. Great advice! Especially when it comes to silhouette. I notice in quite a few (so-called well dressed people) the lines of the apparel are not in harmony with the shape of the shoe.

  4. Low_profile – Yea, it completely boggles me how so many people can just forget about the shoes yet spend so much on everything else. For me, the style starts at the feet and works up! Thanks for reading.-Justin, "The Shoe Snob"

  5. I really love your site as I am a shoe "whore", LOL. Your taste is impeccible….however, I do disagree with a few of your comments. In certain shoes I do prefer a higher heel such as the one you showed as a Salon shoe. Actually, I think of it as quite elegant. I also prefer an elongated toe in many of my shoes, but I guess that is a personal choice—not so out there, but probably more elongated than most would prefer. In any case, thank you for all of your advice on your site, and good luck with your future endeavors in creating your own line.

  6. william hinsberger

    Ouch! The over 50 comment really hurts. Men’s shoe styles have not really changed much over the past 100 years. Go back & look at all the shoe styles, only subtle changes have occurred. What was once old is now new, you will understand….when you turn 50.

    1. yes, this post is a bit outdated and I was a bit fresh behind the ears when i wrote it. I have not edited it, particularly after having moved to Europe, where it is mainly the men over 50 who are the smart ones….nice come back though on that last phrase, I deserved it!

  7. Classic is always The way to go, The styles that emerged 100 years ago are pretty much the same working today with a little up date, no matter if you are 21 or 71 a good handmade calfskin classic will always be a smart choice

  8. Surely the first and most important thing to get right when buying any type of shoe is the fit??Love the blog!!

  9. Hi Shoe Snob. Very useful article.

    But you have written “you should not be wearing heels that are much higher than 3cm or 1.2in.”

    How do you measure the heels? I mean because they are slanting therefore their height will vary from one end to another.

    Also, some people say one should deduct the thickness of the sole from the heel. Is that right?

    1. Dear Farhan, it is rare that heels slant in RTW footwear…that is more common in bespoke and well for bespoke there are no rules…it will depend on what your foot needs..but to answer your question, you measure them from the very back part (the highest part) and not you should not deduct the sole, that is part of it all

      1. Thanks mate.

        Actually yesterday I bought a pair of black plain toe oxfords with high heels. After buying them I felt the heel is too high and searched online and came to your site.

        They have some slanting. The highest part of the heel is 3.6 cm. and the lowest part is 3 cm. I am 5ft 8 inch tall and these shoes make me look feminine. I suspected something is wrong with the heel and you vindicated me.

        Thanks again, I’ll get them changed.

  10. Sure those big heeled shoes look a little odd from the side at eye level, but who ever actually looks at a shoe like that when you’re wearing it? Also, couldn’t taller people get away with slightly bigger heels?

  11. Need some help I bought these To Boots New York Cap Toe Brandon -Cognac- shoes and was wondering what I should do because breaking them in (2nd day) is hurting bad. Not sure if the salesperson sold me shoes too small or not, but it really hurts around the laces. Any suggestions would be great to either go up 1/2 a size or just suck it up and give up the shoes

    1. sounds like they might be too small or you have a really high instep as from what I know of To Boot New York shoes, they are quite soft, so if they are really uncomfortable, then something is wrong…did you get them at Nordstrom?

  12. thanks to this site i wont look Like a clown no more…

    any tips how to match socks?

    any good brand and style under $300
    what style and brand are does black and suede
    sorry if I ask to much do not want to dress like a clown any more lol

  13. Need help identifying the brand of dress shoes I bought today. Brand wore off. All it says on the shoe is genuine leather upper, bal qual man made mat’l. Then a whole bunch of numbers

    1. I hope you found an answer, because all I had to do was google those weird words and it said Thom McAn. It was a listing on Etsy. Someone was selling an old pair of shoes and wrote what it said inside: “Comb Genuine Leather & Qual Man Made Mat’l Bal Qual Man Made Mat’l 2R5 T70030 EJ 66277 187”.

  14. Jamie Saunders

    Hey, Nice article, I have never been able to purchase a shiny pair of shoes since graduation. I think I can give it a try now.

  15. Jonathan Goldsmith

    Have you tried the upper ranges of Loake shoes made in Northampton?? There is a great place in Aldgate, London E1, City border near Liverpool Street Station, where they are heavily discounted… Check them out… XENLondon… in Harrow Place, E1. Website is

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