The Day I Bought the Worst Shoes in the World
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by James Gallichio

I’ll let you in on a little secret: I have made many a style faux-pas in my life.Now I know what you’re saying; “what? I don’t believe that for a second, James. You were always cool!”
Thanks. I appreciate that, dear reader. Very kind of you to say. But truth be told, when a man is young and heading out into the world, the time is ripe for experimentation, fashion (or other)-wise. Experimentation is good; it pushes your boundaries and it tests new waters – but, as with all experiments, mistakes can happen. This is the story of one of them.
It was a Thursday. Winter. Melbourne
I had a bit of spare money and wanted to get some new shoes. I had never had a nice pair of leather shoes, you see, so I sought to fill this gaping hole in my wardrobe.
On the advice of a couple of friends, I decided to check out a certain Chapel St store, which will remain nameless. They were having a special deal (which I suspect they have all the time, by the way, but I’ve been too damaged to go back): 3 pairs of shoes for $140.
“$140 for 3 pairs of shoes?! That’s like…$23 per shoe!”
What an amazing deal. I went inside, and the sales woman immediately began trying to guess my horoscope.
Me: Hey, I’m after a pair of shoes.
Her: Which ones do you like?
Me: Uhh…how about these?
Her: Oh. My. God. You are such an Aries!
Me: …huh?After much picking and choosing, I decided upon 3 pairs of shoes. Unfortunately, I didn’t keep them for very long, so was unable to snap a photo of all but one of them. Rest assured, however, that they were the worst shoes in the world. Here is a short descriptor of each:
Shoe One:
The least offensive of the three; a black faux-leather shoe with a slightly squared-and-a-little-too-pointy toe.
Shoe Two:

It pains me to say it, but yes. I did it. I bought these shoes (see left). I apologise for every buying these. White faux-leather loafers, with a long, square toe. These are bad shoes for many reasons, least of which is the fact that the toe curls up. Avoid these shoes and any shoes that look even remotely like them.Shoe Three:
Thinking about Shoe Three still gives me chills. I never wore them once (I swear!), and I wish I had the foresight to take a photo before I donated them to charity (who, in turn, probably threw them away). They were brown, stiff, faux-leather shoes with a long, square toe. They were “painted” with some sort of brown spray paint that kind of sparkled in the right light.
Many men have trouble understanding the difference between a good and bad shoe – god knows I did. So I will lay out exactly why these shoes were poor choices:
What I did wrong…
Next time I should..
They were all tacky, cheap, faux-leather Spend my money on 1 high quality pair of shoes, instead of 3 pairs of cheaply-made shoes. They all had long, square toes Choose shoes with a classic shape (see here and here). One was white leather with a long, square toe – the trifecta of bad. Slap the sales assistant for suggesting that I buy these shoes. The silver lining, of course, is that I made these mistakes so that you don’t have to. I wore those white, square-toed leather shoes a couple of times and, to say the least, people didn’t respond kindly to them. The big lesson here is that a square-toed shoe is just wrong, and should be avoided at all costs. It’s comparable to having a triangle-toed or hexagon-toed shoe; why would you do it? The classic, round toe has been around for centuries and isn’t going anywhere. Round-toes make great shoes; square-toes make tacky shoes.
So there you have it – the story of the time I bought the worst shoes in the world. I make no excuses for my fashion experimentations, as they’re an important part of carving out your own personal style. And now, thankfully, I know better.
For an in-depth look at what makes a good shoe, check out our Four Shoes that Every Man Must Own and Real Men Wear Boots articles.
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