4 Biggest Men's Dress Shoe Mistakes

The 4 Biggest Men’s Dress Shoe Mistakes & How To Avoid Them

The other day, I visited the VW Phaeton manufacturing plant in Dresden, Germany. The facility is absolutely beautiful and the cars they assemble there are the VW Phaeton as well as the Bentley Flying Spur. The workmanship of these cars is top notch and they really spent a lot of money to have everything look first class. At the same time, the people they employ wore those cheap square toed shoes that just scream amateur and overall, it made their product look less sophisticated.

The same is true for you. People may think less highly of you simply because you wear ugly shoes. Therefore I created a video about the 4 Biggest Men’s Dress Shoe mistakes and how you can avoid them so you present yourself in the best possible way.


Now that you’ve mastered the three most essential shoes in a man’s shoe closet, it’s really important to avoid certain things.

Square toe monk strap shoe from Harry S. Truman

Square toe monk strap shoe from Harry S. Truman

1. Don’t Wear Square-Toed Shoes

First of all, do not buy square-toed shoes and by square toed shoes, I don’t mean the fine chiseled toes from English shoemakers. I mean these kinds of ugly shoes with rubber soles, big, chunky toe boxes and they simply make you look like a peasant. They’re clunky, they’re not elegant, they’re not stylish and it doesn’t matter if it’s a lace-up shoe or sometimes they come in loafers with like elastic sides. They look horrible and you should avoid them at all cost.

2. Do Not Buy The Same Shoe Twice

The second thing you shouldn’t do is to buy the same shoe twice or the same shoe in a different color. I hear you, you just got a pair of shoes and you really love it. It fits well, it looks good on you, why not buy a second pair you might think.Yu are at the beginning of building your shoe closet and maybe if you already have three pairs of shoes, you can buy a pair of the same shoe but if you are not there yet, what you should do is buy one style at a time because that gives you more versatility and different looks. if you buy a quality shoe, you can wear it long enough that you shouldn’t need a second pair which is exactly the same or just the same style in a different color. What you can do is you can get something on the same last but it being a different shoe and that’s definitely something to consider because if the fit is right, you want to keep that fit but you want to change the look.

Casual Cap Toe Oxford with metal eyelets and rubber sole by Sanders

Casual Cap Toe Oxford with metal eyelets and rubber sole by Sanders

3. Avoid Rubber Soles

Third don’t is to avoid rubber soles. Dress shoes are dressy and you want to have a leather sole because when you walk it gives that really elegant sound and they may be a little more difficult to maintain but a good leather sole won’t let water in even if it’s raining and if you live in an area where it’s really wet or the winters are long, you can get rubber galoshes to wear on the outside and then take them off when you’re inside.

Pediwear Collection Black Cap Toe Oxford - True Budget Oxford at 109.50 GBP.

Pediwear Collection Black Cap Toe Oxford – True Budget Oxford at 109.50 GBP.

4. Stick To The Basics

Four, don’t buy shoes that are too colorful in the beginning or too unusual. Skip the spectators, skip dark green or blue shoes when you’re just starting out. Even though they may be 80% off and on sale and you may like the look, at the end of the day, you’re not going to get a lot of wear out of them and they’re going to stay in your shoe closet and the cost per wear goes up. Invest wisely, take a look at your shoe closet and see what you have. Oxfords or Derbies are always a good start.

If you don’t have the styles I recommend, I really suggest you take a look att them and I promise you, it will help you to create a long lasting versatile wardrobe that is elegant and stylish for the foreseeable future.

If you enjoyed this video, please sign up to our email list and I’ll send you more of these videos right to your inbox and check out our website www gentlemansgazette.com where we have a lot of material all about classic men’s clothing and style.Thank you!

25 replies
  1. David Cleland says:

    Sound advice and some I have been giving to young attorneys for years. You can always tell the recent grad by the shoes he wears! Thick, black, rubber bottom Cole Hann shoes scream failure!

  2. Sirtnn says:

    I thought you were going to mention:
    1. Unpolished shoes. All too often shoes that aren’t polished seem to reveal more about the man than most other clues. Whether be brushed them himself the night before or paid a kid at the sidewalk a polished shoe makes the right statement.
    2. Wearing the same shoes 2 days in a row. Give your shows a days rest and they will reward you with years of service. Shoes need to breathe after a wearing to regain their shape, air out any smell, etc. and that leads to #3
    3. Not using shoe trees. These are essential for keeping your shoes in tip top shape. Gently slide them in when you remove your shoes and they help form the shoe back to its natural state. They also absorb sweat Some travelers stuff their shoes with rolled up socks, underwear, hanki’s, etc and avoid using shoe trees when traveling to save on weight and space. While this works from a packing perspective if you’re needing to wear them more than once it’s better to pack them with their shoe trees, your feet will thank you.
    4. Not replacing the heels or soles when worn- Granted every politician proudly displays the holes on the bottom of his soles before the election to indicate he’s been hitting the streets with the common man, it just doesn’t make sense to let your shoes wear out and not take care of them. New heels and or soles also are much more comfortable than maneuvering sidewalks and puddles in shoes that need some tender loving care.

  3. Rufus T. Firefly says:

    Well, while there are certain classic rules of dress that seem timeless ultimately taste is an individual’s prerogative. I agree that many square toed shoes are clunky and unattractive but all are not necessarily so “peasant”. Some shoes with a squared off toe are actually quite elegant. As for rubber or synthetic soles, again I feel you are being quite unfair. Leather soles can be less comfortable and certainly can be unsafe in winter conditions. Today many rubber/synthetic soled shoes are just as attractive as leather and far more comfortable on the feet besides being at times more durable. The fact that you are very opinionated makes your contributions fun to read and usual I agree with them. However here I respectfully disagree.

      • KC says:

        Magnanni has the best elegant rubber soled shoes. They are very comfortable and very stylish.. I think they are the exception!

          • Erik Wilgenhof Plante says:

            There’s two reasons I don’t want to wear leather soled shoes. The first is that I need some shock absorbing quality in my shoe due to health reasons. The second is that I live in Singapore where the humidity destroys any shoe within a year. Unless I’m suddenly a billionaire, I’m not going to dedicate a climate controlled room to my shoes.

            • Sven Raphael Schneider says:

              Why would humidity destroy a quality shoe? I have been to many areas with humid cliamtes for an extended period of time without any problems.
              Some shoes have some shock absorbers on the inside but if that is really a concern you should look into custom inserts rather than rubber soles.

  4. Denys D. says:

    I wholeheartedly agree with you on most points you made, with the possible exception of the third point, that is, avoiding rubber soles. While I appreciate the leather soles, personally, I can’t just wear such shoes and go off onto the street. There are two reasons for this: first, as Rufus Firefly mentioned above, they have very little traction on some surfaces (and I mean smooth/tiled floors found in many public places, as well as during the winter); and second, which is something psychological, I shrivel at the idea of damaging the leather (however treated and hardened it might be) by scraping and stomping on the rough and gritty pavement. Therefore, I always take leather-soled shoes to a cobbler and ask him to put a thin (about 1/16″-1/8″) ribbed rubber patch on top. It doesn’t only preserve the shoe but provides better traction.

    Actually, another point I want to make in this regard, I feel it’s important to consider the welting type of a leather-soled shoe. With Blake welting you may leave the sole as is and not worry much about it, whereas with Goodyear welting, where the stitching is exposed on the bottom, the shoes may require more sole maintenance and care to prevent a sudden ripping of the string. This is another reason why I believe the rubber patching of the soles may be warranted.

  5. Boswell says:

    Come to Australia and you’ll witness the ugliest shoes on the planet. They can be seen everywhere – in the business precinct, at the mall, on the streets – everywhere! And they can be seen worn by even the wealthiest master of the universe types and by men who otherwise are dressed quite well up top. I don’t mean square toes, which bloggers keep hammering on about, but the ugliness I am referring to are shoes with very pointy ends made from poor corrected grain leather, and especially shoes that have a very low slung silhouette with a chisel square end that curls up.

  6. Jean says:

    Dear Sven

    “You can be perfectly well dressed without spit polishing your shoes every time.” (Sven Raphael Schneider says:
    August 12, 2015 at 3:32 PM)
    You weren’t in the military-service, were you? Shoes should always be spit-polished!! It shows one pays attention to ones gear.

    Rubber Soles: I’m with Dennis D.:
    I buy leather-soled shoes and their first trip is to the repair-shop to put some thin ribbed rubber on them: Leather-soles are far to slippery on certain pavements (cobble-stones are a nice example). I know people that do the opposite: They buy cheap rubber-soled shoes and have the repair-man put some thin leather soles under them (that’s pure snobbism!)

    • Sven Raphael Schneider says:

      Spit polish is one way to polish shoes and while it has its plays it is not a requirement of being well dressed. Just because a superior in the military required you to do it does not mean that it is the only acceptable option in real life. If you like spit polish, go for it but in order to do it properly you need several minutes, and it is not always feasible, not it is desired for every kind of outfit.
      Rubber soles are for certain country shoes, not for dress shoes.

      • LB says:

        You’re right. I am an ex-soldier, but spit-shined or bulled shoes can be a bit too much. And it looks rubbish on suede :).

  7. Andrew says:

    I agree with your thoughts about square pointed toes. However, there are many shoes out in the market that are too pointy. I don’t want to look like a peasant but I also don’t want to look like an elf. What type of toe styles do you recommend?

  8. jo wilkinson says:

    Sven, all correct bar the rubber soles. Better for the feet through cushioning effect, it has greater flexibility than heavy leather but most of all is grip. In wet conditions particularly, rubber is superior, plus it is waterproof, whereas leather becomes waterlogged. In the office environment leather may be superior but if one has to walk more than a few hundred yards rubber is superior. Elegance can live in a vacuum, great in a photo shoot or ball but for the everyday style must also endure. Many European brands, Zegna, Tod’s, Ferragamo, Gucci etc. have been moving to rubber soled dress shoes for these reasons. It’s no longer considered less stylish, its about pragmatism and the modern male uniform; for example as much as I admire pocket squares few world leaders or top businessmen ever wear them. Its the same philosophy for rubber soled shoes.

  9. michael snow says:

    It’s all very well saying ‘no’ to this, that and the other, but when you have feet the size & shape of mine, in the UK you have four choices

    Any suggestions (that don’t involve spending £1000s on hand-made shoes)?

  10. Scott says:

    I own a lot of shoes. I have my dress and casual shoes covered this season, so I’ve starting to buy some shoes in different colors; burgundy, dark green, dark blue, etc. They add a lift and smile to my day as long as I don’t wear them too often and become “That Guy” with the weird shoes.

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