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Why Buying Cheap Shoes Is So Damn Expensive

If you had to rank your suit, shirt, tie, pocket square and shoes on a scale of 1 to 5 (as in 1 most important and 5 least important), what would your list look like?

Without ever laying eyes on you, I can tell you with 100% certainty whether or not you have a great sense of style. And it’s all based on how you answer this very question. Let me show you how.

As a Wardrobe Consultant/Personal Shopper, part of my job is speaking to clients about their budgets before going out on the field (more on that later).

One thing that never ceases to amaze me is how many men still think of their shoes as just a necessity, instead of the most crucial part to their outfit.

Allow me to elaborate further…

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Regardless of relationship status and/or sexual orientation, few things are more flattering to a man than getting a compliment from a woman.

The vast majority of comments that I’ve received from the opposite sex has to do with my choice of footwear.

BONUS: DOWNLOAD THE FREE LIST OF THE TOP 5 SHOE-SHINING TOOLS I USE TO KEEP MY SHOES LOOKING NEW.

Now we’ve all heard the saying that the first thing a woman notices about a man is his shoes.

Something tells me that whoever came up with said phrase wasn’t referring to a pair of sneakers.

I’m not passing judgment on what another man wears or how he spends his hard earned money (maybe a little).

But one thing that I take an issue with is how a lot of men would rather wait on line for a pair of sneakers costing upwards of $250+ and then say that good dress shoes are way too expensive.

Don’t get me wrong, I was never a sneakerhead. But I had almost every pair of Jordans that came out throughout my high school and college years.

But now as a man in his thirties, I’m having a hard time understanding this logic.

"That’s at least $350 in 2 months on something that you can’t wear to a job interview, a wedding, most jobs, etc."

Let’s do the math real quick, you shell out $175 to $200 for a new pair of retro J’s, cool. Then 2 months later, another pair comes out and it’s another “must-have” for your collection, so you buy that one too.

That’s at least $350 in 2 months on something that you can’t wear to job interviews, weddings, most jobs, etc.

But you think that paying $400 for dress shoes that are acceptable for practically any occasion aren’t affordable? Give me a break!

The funny part is Nike keeps recycling the same sneakers. They know that the quality of their product is mediocre at best.

They know that there’s no way that you still have the exact same pair from when they released them just 2 years back. They know that you will buy them again.

Recently I was feeling a bit nostalgic and pulled out one of my old pairs from about 15 years ago that I hadn’t touched in at least 10 years.

But I had them freshly kept (so I thought) in its original box. Well, you can see the results below.

What Constitutes A Good Shoe?

There are plenty of articles on the web on that very subject so I’m not going to spend a lot of time on it here.

You can check out the 3 Part Series ‘Things To Know About Shoes’ from the self-proclaimed Shoe Snob turned respected Shoemaker Justin Fitzpatrick for more insight.

But just to summarize:

  1. Construction: Goodyear welted shoes allow for them to be re-soled rather easily by a skilled cobbler once the sole wears out. Cheaply made shoes, on the other hand, are usually glued together as opposed to being stitched.
  2. Leather: Quality shoes are made from a high-grade leather instead of a corrected grain leather. Corrected grain is a leather that’s smothered with chemicals to hide its flaws.
  3. Aesthetics: This one is the easiest to determine with the naked eye. I’m referring to how the shoes look. That consists of the shape (which is called the Last), the design, the style and so forth. But be aware of shoes that are made in a decent shape but are glued together and use bad quality leather.

I Can Hear You Now, If Quality Shoes Are So Great, Then How Come More Men Don’t Buy Them?

From speaking to a few of my clients, colleagues, and friends about this subject, I came up with a few reasons.

BONUS: DOWNLOAD THE FREE LIST OF THE TOP 5 SHOE-SHINING TOOLS I USE TO KEEP MY SHOES LOOKING NEW.

Here are my Top 7:

1. COMFORT

Next time you’re at a department store and see a man trying on some shoes, pay close attention. You’ll notice that he flexes them by making the toe box touch the back heel.

Something that’s nearly impossible with a Goodyear constructed shoe.

I don’t know what that accomplishes. But if you ever find your shoe in that position with your foot still in it then you’re in major trouble.

Some refer to shoes as hard bottoms. And that doesn’t sound the least bit comfortable. The misconception is that the sole of a well-constructed shoe is made out of wood.

But in reality, most shoe bottoms are also made out of leather but painted to give the appearance of wood (see below).

The shoes that the majority wears are usually slip-ons and go on and off with minimal effort. And one point that they always stress is how comfortable their shoes are.

I’m not saying that good shoes are uncomfortable, the opposite actually. But I don’t think that comfort is at the top of the list when a shoemaker is designing his shoes.

Welted constructed shoes can be a little stiff in the beginning. Some may require a break-in period before fitting you like a glove assuming you bought the right size.

2. PERCEIVED VALUE

I think that 90% of men don’t see enough value in a $350 to $400 pair of quality shoes.

That train of thought is due to the fact that they can buy a pair from Sears that serves the same function (so they think) and save $300 in the process.

But are they really saving that much if any at all? Doubtful.

A co-worker of mine once told me that he bought his shoes on sale at Sears for $75 and saved $10 off the regular price. He was so proud that he took them off to give me a closer look (see below).

He said that they last anywhere from 9 to 12 months before the sole wears out and the stitching in the upper starts to pop.

So some simple math tells us that every 5 years, he’s spending anywhere from $375 to $425. That’s higher than the $350 to $400 price point for nice shoes.

And not to mention walking around with shitty shoes for 5 years, missing out on all sorts of compliments.

A Goodyear constructed shoe will last you anywhere from 10, 15 to 20 years and beyond, assuming you take good care of it. Which takes me to my next point.

3. MAINTENANCE

Good shoes need to be cared for like anything else worth having to keep them in tip-top shape. And most men are not willing to put in the work required to accomplish that.

A beautiful woman goes to the gym, eats right and gets her hair and nails done to maintain her beauty.

Similarly, shoes need to be fed its nutrients to keep its skin healthy and get brushed after each wear to get rid of dirt that it collected throughout the day.

You also need to buy wooden shoe trees to insert in them right after taking them off to absorb the moisture.

And just as important, you must use a shoe horn when putting on your shoes so you don’t damage the leather with your heel.

BONUS: DOWNLOAD THE FREE LIST OF THE TOP 5 SHOE-SHINING TOOLS I USE TO KEEP MY SHOES LOOKING NEW.

4. MONEY (or lack thereof)

There’s really no way around this, some people simply don’t have $300+ to drop on shoes. I’m very cognizant of that fact.

The reason why I didn’t put it #1 is because I’m not really speaking to that crowd. I’m more referring to the guy who spends the same or more on sneakers and a Gucci belt.

5. CARELESSNESS

Unfortunately these days, a good portion of men can really care less about their appearance.

Wearing shoes is just a way for them to cover their feet since going to work or an event in sneakers or barefooted isn’t an option.

So they go with the cheapest option.

6. BAD TASTE

This one is self-explanatory. Let’s face it, some men just simply have bad taste.

Squared toe shoes that make them look like they have elephant feet is just their preference.

In their eyes, those types of shoes look good and you can’t convince them otherwise.

7. IGNORANCE

Last but not least, I think that the majority of my fellow men out there have no idea what makes a shoe ugly or beautiful.

They don’t have a clue. They’re more focused on the other parts of their ensemble to worry about their shoes

Which Brings Me Back To The Whole List Thing. Remember The List?

I’ve had more than a few clients break down their list (see bold) and shopping budget as follows:

(I’ll use $1,000 for this example)

  1. Suit: $700
  2. Shirt: $75
  3. Tie: $50
  4. Pocket Square: $50
  5. Shoes: $125

They justify their subpar ranking by saying that shoes aren’t as visible as the upper half (jacket, shirt, and tie) so they shouldn’t command the same amount of money and/or attention.

"Way too many men treat their shoes as an extra on a movie set. Liable to be left on the cutting room floor."

To that I say, unless you work out of your car and never have to step out of it then that logic is flawed.

BONUS: DOWNLOAD THE FREE LIST OF THE TOP 5 SHOE-SHINING TOOLS I USE TO KEEP MY SHOES LOOKING NEW.

The problem is way too many men treat their shoes like an extra on a movie set. Liable to be left on the cutting room floor.

One of my Asian friends once told me in jest that the reason why they bow their heads in his culture upon greeting someone is so they can check out the other person’ shoes.

I’m sure that he was joking but still.

Now don’t get me wrong, I’m very sensitive to my clients’ finances but there are better ways to do this.

As you can see in the example above, the shoes were an afterthought and only came into play once everything else was accounted for.

I understand cutting corners to fit within’s one budget but skimping on the most important part of your outfit to accomplish that goal is hardly the way to go.

What I’d propose in this situation would look more like this:

  1. Shoes: $325
  2. Suit: $500
  3. Shirt: $75
  4. Tie: $65
  5. Pocket Square: $35

As you can see, I got the shoes out the way first. Shoes are always first on my outfit hierarchy (see bold).

Then I worked everything else in with the remaining balance.

What I’m really saying is, you can get away with a cheaper suit ($400 – $500). As long it fits well and you accessorize it with a clean shirt, a nice tie and pocket square.

But wearing your ugly and poorly made shoes brings everything crashing down regardless of what the rest of your outfit looks like.

"My shoes are the star, my suit and tie are the co-stars and my shirt, socks and pocket square are the supporting actors."

I treat getting dressed like shooting a Hollywood blockbuster.

My shoes are the star, my suit and tie are the co-stars and my shirt, socks and a pocket square are the supporting actors.

I’ve heard many stylish men refer to their shoes as the anchor of their wardrobe and I couldn’t agree more.

Shoes are to an outfit what the foundation is to a house.

BONUS: DOWNLOAD THE FREE LIST OF THE TOP 5 SHOE-SHINING TOOLS I USE TO KEEP MY SHOES LOOKING NEW.

No one in their right mind would get their kitchen renovated with all new stainless steel appliances and granite countertops knowing that the foundation beneath it is crumbling.

Think about that next time you’re putting your list together.

Where Not To Buy Your Shoes?

So you decided to step your shoe game up and you’re ready to start shopping. Whatever you do, don’t go to your local mall and department stores for a few reasons:

  1. They’re way overpriced.
  2. You’re paying for the name and not the quality.
  3. You won’t find anything in that sweet $350-$400 price range.

To Wrap It Up…

A pair of nicely made shoes with a good shine is a sight to behold. Does wearing cheap ugly shoes make you less of a man? Absolutely not.

But there’s no reason why you shouldn’t have at least one good pair of shoes in your closet.

Hopefully, this article will help some of you make that transition. The ladies are waiting to throw some praises your way and what’s better than that? Cheers!

  • Pete Ferriello

    Thanks for this piece. I enjoyed reading it and it’s changed the way I think about my shoe game.

    • Thank you for reading it, Peter. I’m glad that it made a difference.

  • george brooks

    Great read. Clunky cheap shoes never looked good on anyone. This article definitely put the importance of a quality pair of shoes in perspective.

    • Thanks for the comment, George and I couldn’t agree more. I’ve yet to see anyone look sharp in one of those. I hope as many men get to read this article as possible.

  • cameron bibb

    Great read! Im neither a sneaker head nor a shoe groupie but this article was informative to say the least.

    • Thank you, Cameron! My goal is to give out useful information with every post. I’m glad that I’m on the right track.

  • Ryan Rubi

    This is awesome. I agree that shoes is number one on the list. I personally would spend $450 on durable and nice dress shoes too. I also like the lapel flower as an accessory with the pocket square and tie bar too depending on the occasion.

    • Thanks, Ryan. I definitely agree that accessories are very important, I couldn’t imagine leaving the house without a PS. I’ve shied away from tie bars though the past few years once they became too trendy. YMMV

  • Raymond Fevrier

    Great article (as usual). My key takeaway was the ‘What Constitute a Good Shoe?’ section, it really did put things in perspective for me. Since we started working together, I became a ‘suit guy’, but as I have told you in our many conversations, I never saw shoes as being on higher pedestal than say a suit. Now I get your point, although a part of me feel they are EQUALLY as important 🙂
    One more thing, where do socks fit into this equation? I feel I get a lot of compliments when I am wearing a nice pair of ‘Happy Socks’

    • Hey Ray, from how low shoes were on your totem pole, to now being on equal footing with a suit is a HUGE win, LOL. I’m a sock person myself although I stick to solid colors and over-the-calf socks. They play a major part when you’re sitting down and bring lots of attention to your choice of footwear.

  • Bill St. Fleur

    Great insight. I particularly like your viewpoints on a good quality shoe being the focal point. I also like to add thay in my experiences to not be afraid of color. Traditionally we’re trained to just go with a standard black lace up. A nice brown, red or even blue tones add an extra touch to allow you to stand out from the crowd.

    • Thanks for the comment, Bill. And yes, shoes come in so many different colors nowadays and having choices is a great thing. Assuming one has the basics covered (Black, Brown and Burgundy), a nice Green or Blue pair in leather or suede definitely works.

  • Claude Laforest

    Tell you the truth I am in the market for some nice shoes maybe 150$-200& the most.

  • YVES CELESTIN

    GETTING DRESSED, IS ALMOST LIKE PUTTING A GREAT BAND TOGETHER. EVERY MUSICIAN CONTRIBUTES TO THE GREAT SONGS AND SUCCESS OF THAT BAND. WHEN ONE INSTRUMENT IS NOT IN TUNE, IT CAN MAKE ANY GREAT SONG SOUNDS MEDIOCRE. SHOES ARE VERY IMPORTANT TO AN OUTFIT. YOU MAY HAVE A GREAT POSTURE AND MAKE AVERAGE SUIT LOOK GREAT, BUT IT’S IMPOSSIBLE TO MAKE CHEAP SHOES LOOK GREAT. BESIDES THE SUIT ITSELF, YOUR SHOES ARE THE ONLY OTHER PIECE OF YOUR OUTFIT YOU CANNOT HIDE. YOU CAN HIDE A BAD SHIRT BEHIND A BEAUTIFUL TIE AND THE RIGHT SUIT, BUT THEY DON’T MAKE SOCKS BEAUTIFUL ENOUGH TO GET THE FOCUS OFF A CHEAP PAIR OF SHOES.

    • Beautifully said, Yves! I couldn’t have said it better myself. Maybe you should start your own blog. LOL

      • YVES CELESTIN

        HAHAHA. I don’t know about all that.

  • Rose Mednard

    Great post! This is an indirect guide of how to get a woman to notice you too. We never miss good shoes.

    • Thanks for commenting, Rose! I’m just trying to help out my fellow men.

  • Chris

    Late to the party! I agree with every single word that you’ve said here, Vlad. Even though I have not purchased anything in the higher end of the good year welts, my Allen Edmonds Strands are already a HUGE difference in quality from the shoes you can purchase at Marshall’s, Aldo, DSW etc..

    Knowing that I can have them recrafted (at a fraction of the cost) and come back looking almost new already made them worth the price I paid. Also, they still look great after about 3 years of wearing to holidays, special events, and even clubbing. Keep up the great writing and good work!

    • You’re 100% right, Chris. You save so much money in the long run with quality shoes plus they look better. It’s a win win.

  • Rocko aka Gary

    Great article my dude! Definitely put things in perspective for me. Now i buy what like……depending on price of course & with a conscience mind. Now as i climb that latter, i feel that and i have to look da part of what community employer preaches. I be the 1 to admit that unlike sneakers, when it comes to shoes, i don’t know what to cop. But like sneakers, i refuse to pay 3 or 4 bills for a pair of kicks. What do you suggest? How about casuual kicks?? I’m in da market for 1 of those as well.

    • Thanks for reading and your kind comment, Rock! I can definitely understand not wanting to drop $400 on one pair especially when just starting out. I can guide you in the right direction in the $200 range and build up from there with brands like Meermin and others. As far as casual shoes, I would advise Suede shoes and Monk Straps. Those type of shoes can be dressed up or be worn casually as well, more bang for your buck.

      Reach out to me directly for more at vlad@chaceandryder.com.

  • Samuel Charles

    Amazing article! I think a lot of times people just do not think this way. I, myself am a victim of not having that mindset. Moreover it’s important to point out that a lot of people when they buy something as expensive only brings that item out for special occasions. For me I think my biggest fear is not buying something for name sake but rather quality! Great read…

    • Hey Sam, thanks for reading and commenting. You’re right about some bringing out their most expensive items only on special occasions. I think the point is to eventually have a nice collection for all occasions so you’re always on point even if you’re not wearing your best shoes at the time. But the key is to start with one and build from there.

      Since you like this post, you’ll definitely appreciate my next one as it is a follow-up to this one. I go into details on what name brands to run away from and where to get the best quality shoes without breaking the bank. So you can put your fear about spending a lot of money mostly for the name brand to rest. You’ll receive an email update in a couple days once it’s published. Cheers!

  • Darrin G

    Great read. I constantly struggle with shoe prices. My budget prevents me from stepping out of the “Macy’s” bracket but I use to love shoes when I had more money and I would spend $300-400 on a pair without stress. Can you recommend a good shoe at a reasonable $150-200 price range or even somewhere that might have an old school “layaway” plan for people on a basic budget?

    • Hey Darrin, thanks for reading the post. Funny you ask because I get this question a lot and I can definitely help. My suggestion would be the classic line from Meermin. I’ll contact you directly to see what exactly you’re looking for.

  • Eddy Cameo

    Preach, Brother! Preach! Oh, and also remind us… and keep me from going back to $100 shoes… sometimes you get tempted when there is a sale… and I justify it, thinking that I can get a few good months out of it. But then, as you just said; I would miss on all the compliments. Thanks for writing and helping.

    • Vladimir Riché

      Thanks for reading, fam! You’re only hurting yourself in the long run and basically throwing $100 in the trash. You’d be better off waiting and try to save up $200 instead. There’s a world of difference between an entry lever quality shoe for around $200 and a pair that’s glued with inferior leather costing around $100.