The 4 Biggest Men’s Dress Shoe Mistakes

The 4 Biggest Men’s Dress Shoe Mistakes

Now that you’ve mastered the three most essential
shoes in a man’s shoe closet, it’s really important to avoid certain things. 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. 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. 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. 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. 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 where we have a lot of material all about
classic men’s clothing and style.Thank you!

100 Replies to “The 4 Biggest Men’s Dress Shoe Mistakes”

  1. Great channel. Square toe shoes are great if you have Egyptian Feet (squared toe silhouette), shoes that come to a point in the center have never been comfortable for me, I don't have elf feet.

  2. Late to watch this video. 🙁 I bought black brogues with rubber soles ( and I don't know what to club them with. Help!

  3. The only shoes that I would consider buying multiples of would be an essential like black Oxfords, but only if you already have a sizable shoe collection already. I wear suits everyday and black oxfords just look good with everything, and Lord knows I hate polishing on weeknights 😀

  4. Shoe companies keep on making square toe dress shoes and dress shoes with rubber soles. I guess consumers want them. I say do what works for you and forget everyone else because you're the one that paid for the items and have to wear them.

  5. Yeah I'd love to get leather soled shoes, but I can't drop $300+ on shoes right now. Many mid-range brands like Florsheim and Stacy Adams make great shoes with rubber soles.

  6. NO SQUARE TOED SHOES! NO RUBBER OUTSOLE! NOW THAT'S WHAT I'M TALKING ABOUT! Square toed shoes are ugly and and rubber soles just don't belong on dress shoes! As well as cowboy boots and other dressy type boots. LEATHER ALL THE WAY!

  7. 0:33 "They simply make you look like… a peasant."

    I literally chortled. I guess that's an "LOL".

    That was hilarious.

  8. No rubber soles? What if you are walking outside and need grip? I remember wearing leather soles when it was icy in the winter, also broke my neck!
    I personally don't have a problem with a vibram sole on my shoes.
    Also, leather soles look grimy if you wear them outside more than 5 times, they start to scratch at the bottom and look messy … Unless you are only going to wear the shoes indoors … I don't see a problem with having a vibram sole on the bottom of your favourite shoes.

  9. What about wearing rubber souls for medical reasons and picking the closest thing to a leather in terms of look?
    Is it OK for business?

  10. This guy hit the spot. I did all of them. #2 Is the mistake that cost me lot of money. I did it twice and where my first expensive pairs.

  11. Darn. I love a good pair of rubber soles and my next pair of shoes is probably going to be a second pair of chukkas.

  12. I couldn't agree with you more about square-toed shoes. I bought a pair some years ago – why, I shall never know – and eventually realized they were so hideous as to be not fit to be seen. Or worn.

  13. I bought my first 2 pair of real shoes recently and wish i had started 20 years ago. The compliments alone from dressing better make it worth it. It's almost like a drug.

  14. I disagree with the leather sole part. There are rubber soles out there that are thin and look very similar to leather soles. The noise that leather soles makes is not cool and can be obtrusive in quiet buildings. Also, leather soles are too slippery in the rain and dangerous. And no I am not going to get galoshes to make life more complicated.
    That said, it's good to own at least one leather sole shoe though because they are still pretty nice.

  15. AZ may be hot, but we average 320 days of cancerous sunshine in the Phoenix area and average 9 inches of rain a year. You can always wear your leather shoes for work, important meetings, dinners, or any occasion that calls for them. I despise rubber soled shoes. They squeak on floors. They're often ugly. Those square toed styles are perfect though for the trip on the Mayflower to Plymouth. I always look at the soles when shoe shopping. Rubber=pass. It seems like leather shoes hold up longer (unless my quick walking pace wreaks havoc on the heel).

  16. What if you are building a professional wardrobe? Don't you want your first three shoes to be plain cap toes in different colors (i.e. a black, dark brown or oxblood pair)? Don't you want to stick to the most conservative look for your first few pairs before you introduce brogues?

  17. I will take the traction of a rubber sole. Leather soles are like walking on a sled. I don't care how good they sound. They are dangerous.

  18. Yeah I know what you mean about shoes. Right now trying to decide between Rockports or SAS. Definitely don't what. To look like a peasant. Might have some other gentleman in jodhpurs ride me down and whip me.

  19. I often agree with this channel but a shoe should be made to fit closely without pointless, excess room. For men, like myself, with very boxy feet, a squared front shoe is the best for comfort and durability.
    Good function will make a shoe much more attractive to the eye of this beholder.

  20. I am sorry, but no; I live in Germany and I am a size 5. In the rare occasion that I can find shoe that fits me, I will buy it twice and in different colors, so that I don't have to go through the frustrating hassle of trying to find shoes again. I do not have the money to have more than one pair made to measure and I am not trying to start a collection of shoes, so I will have to disregard that second rule.

  21. i have over 30 high end suit and close to if not more shoes.. I just got an amazing pair of
    Mezlan Marini in a unique shade of blue.. how would you recommend wearing them?.. I have paired with my jeans and a nice blazer and shirt… and also have worn with a full black Armani as well as a silken black Gucci suit.. however I'm considering the option of different colored slacks? my wife is great and I love her but she will tell me anything looks good so.. HELP?

  22. Being in a tropical country with rainy seasons, I personally prefer rubber soles over leather (or leather soles covered by rubber) as it is more functional

  23. The shoe you showed is exactly what I have as dress shoes and as a tall slender mani get complements on them a lot. I would like more shoes but I feel like your classification of square is too broad

  24. I'm afraid i completely disagree about the rubber sole comments. Most of the highest end British shoe makers offer even the most elegant styles in a Dainite sole. Dainite has a similar flex to leather, and allows an elegant looking shoe, but maintains water resistance. Here in the UK its wet A LOT, and leather soles wear through extremely quickly. Dainite for anything other than summer shoes is a must IMHO.

  25. Watching these videos has made me realize how advanced and how mature my dress up clothes are for being 17.

  26. what would happen to me if I looked like a peasant? could someone let me know urgently please. I have an interview tomorrow and am intending on wearing square toe rubber sole shoe. please you tubers I need your help


    Is this man a peasant? I don't think so. But, I get what you say though. Pres.Obama's shoes here are much more subtle than the square's you have in your video. In the world of symmetry and proportions anything that runs along the frame of your feet its norm. Any line that runs too divergent, makes it look artificial, thus less tasteful.

  28. I make all 4 mistakes.  No wonder I'm still single :[

    Time to buy non-squared shoes once with leather soles that are non-colorful!

  29. first one was a opinion.
    second was common sense.
    third is when you have enough money for rubber covers not rubber soles.
    four well…..of course.

    …..this is some odd advice

  30. Leather soled shoes with a cork filling become very comfortable after some wear, far more comfortable than rubber soled shoes can ever be.

  31. Looks guiltily at the cheap alfani shoes with the square toes rubber soles and elastic on the opening that are in my closet…..sigh I suck.

  32. This man is an IDIOT! Pointy toe shoes are trash and the people who ware them are consumer programmed idiots who are out of touch with reality as to what a human foot looks like.

  33. I like the idea of dressing well but don't like the idea that makes you think dressing well will make you better than a peasant. Makes me think this whole idea of being a gentleman is overrated. People are better by character and not by what they wear.

  34. Out of all the shoes I tried only a pair of squarish shoes didn't irritate my feet. So is your suggestion I shouldn't buy squarish shoes at all and rather buy uncomfortable but more stylish shoes?

  35. It's worth having some smart shoes with rubber soles if you work in particular environments, for example where you may have to move frequently between an office and a factory floor that's covered in dust and oil, or go outside where it's wet. It's not always practical to switch shoes or wear overshoes.

  36. I have to disagree with the 2nd point. I like owning the same shoe in black and brown. I like being able to wear the exact style shoe i want no matter what colors I'm wearing. No one will ever notice in a million years, and if they do, who cares?

  37. nothing wrong with square toe shoes, they add a little edginess to the dress aspect of them, and have a classy look. Id rather have rubber souls because if you ever have to break out running, and you have leather on, you'll enfdup on your arse. Snobby lawyers and big timers dont have to worry about this because they never have the need to break out running, so yall enjoy yall lady leather sounding souls lol

  38. I have dress shoes that are over 25 yrs old – Allen Edmonds shoes can be rebuilt by the factory for a reasonable fee. I also have several pairs of classic hand-made Nettleton wingtips, which are over 50 years old and belonged to my father – it’s kinda cool and special that I can wear the same shoes, that as a boy, I once spent an hour every Sunday evening, polishing for my dad, that he would wear that coming week. Learned about the benefits of using cedar shoe trees, of polishing them by hand, of wearing overshoes when there was inclement weather and the importance of having multiple pairs of shoes, so that each pair can “rest” and not be worn day after day….

  39. I bought a nice pair of dress shoes off eBay and the insoles had been removed. Is there any reason you can think of for doing this? I did insert some dr Scholls insoles.

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