Shoe Journey

When you read any menswear blog or any book from a menswear writers (Bruce G. Boyer, Alan Flusser, Bernard Roetzel, Hardy Amies and so forth), they will tell you to invest in good shoes. That was something that really resonated with me. Why? Because I always say that the things you use the most should be the best, in my case: bed, bureau(chair) and shoes.

Before I knew it I was in a ‘good’ shoe store looking at my first pair of real shoes. I had read a lot of good things about Crockett and Jones. The pricing was steep, especially for a low-earning student. After trying some pairs I felt that they were worth it. The leather was super supple, and when I put my feet in them they really gave support.

I eventually settled on the Crockett and Jones Ashdown. A nice country derby. For a first shoe it’s pretty versatile. I can wear it in the rain, with semi-formal combinations. But also with more ‘rugged’ outfits.  I would not wear them with suits.

There was only one issue: I didn’t know how a proper shoe should fit. So when I walked on the shoes I worryingly told the salesman that I could feel my toes at my right foot hitting the side. The salesman told me that I had to ‘break the shoes in’, afterwards the problem would be gone. I had my doubts but I trusted the salesman, because he should know…right?

After three months of regular wear with painful toes I knew that this issue would not go away.

I had bought my first pair of real shoes, but half a size too small! I went back to the shoe store. After my explanation, they told me to stretch the shoes a little bit. I should come back some days later. I went back, tried the shoes on and the problem was still there. So they tried again, and again the problem was there. In the meantime three months passed. After my third visit they told me they would sent them to the original factory in England. When they came back (eight weeks later) the problem was still there. So after some debate and an e-mail they told me to bring the shoes back so they could order half a size bigger. After waiting a few months I got my shoes! This time in the right size. I was happy and I had learned a valuable lesson! Never blindly trust the salesman, and make sure that the shoes fit from the moment that you put them on in the store.

Over a period of two years I bought my whole shoe wardrobe.  

In order of first to last:

  • Black Alden tassel loafers

I bought these shoes via the internet, a very bad idea! Whenever you can try on the shoes do so! The shoes were nice, but my right foot was not really comfortable.

  • Crockett and Jones Tetbury in dark brown suede

I bought these shoes in a reputable shoe store in Amsterdam called ‘Sir Max’. Alas they are permanently closed. The fit is great! In most circles this is considered the most versatile autumn/winter/spring boot.

  • Sir max (Carlos Santos) brown oxfords

I chose these over the brown Crockett and Jones Hallam because I preferred the colour. Now I know that was a bad call: after some breaking in I discovered some fit issues. The right foot didn’t fit me exactly and there was a little bit too much room at the vamp (where your foot bents). So after long hours of walking the top of my big toe gets really irritated (read: blisters).    

  • Crockett and Jones Cavendish in burgundy cordovan (better fit than my tassels from Alden)

These shoes were expensive, but I really wanted a tassel loafer in cordovan. What better way than to buy them in the official London store. The salesman looked at my feet, and he told me my right foot was almost half a size bigger than my left foot. I totally had no idea. That explains the issues I had with my right foot… So I tried on the shoes and after some walking around in the store they felt really good. I knew I had to buy them!

I wear these shoes a lot!

  • Crockett and jones Connaught in dark brown suede

I also bought these shoes when I was in London. They had a 30% discount on them. Fit is good. When I wear these for a long time I get some irritation at the vamp. But the toe area is long enough, so no issues with my right foot.

  • Crockett and Jones Vincent in snuff suede

I should have learned that buying shoes via the internet was not a good idea. But I did not…(noticing a trend?) I needed a summer loafer, what better way than to order these shoes. They had a 50% per cent discount on them…a nice bargain! So I bought them immediately. After some walking around I had the right-foot-issue again. So now I have these shoes, they look nice. But I cannot walk more than an hour on them…Should have bought the snuff suede Cavendish instead…

  • Trickers white buck derby’s

After the CJ Vincent I should have learned that buying shoes via the internet was not a good idea, and…I did not. These shoes were also on a 50% discount. When I looked at the photo’s I said to myself: “these will fit.” Of course they did not. Really need to sell them…

What I have learned:

  • Never blindly trust salesmen.
  • In my case never buy shoes via the internet (unless I know that the shoes will fit me because of my history with the same last/shoe).

Some question you can ask yourself when buying shoes, in no particular order:

  • Do they fit?

Of course the most important question when trying on shoes… Take in account that your feet may differ in size.

  • Do I like them?

This is something you need to find out for yourself. What do I like? Imagine yourself wearing the shoes, and take a look at which outfit(s) will go with the particular pair of shoes, which takes me to the next point:

  • With which outfit can I wear them?

A derby is easy to wear with more casual outfits, but not with formal outfits (think a formal suit). An oxford is really nice to wear with more formal outfits. Of course there are more factors at play here. A smooth leather derby for example is more formal than a suede oxford. The shape is also important. When they are more elongating (think a chiselled toe, like George Cleverly), they are more formal. When they have a more rounded toe (CJ Connaught) they are more informal. There are a lot of guides about shoe formality, so I don’t think I need to write what others have already put onto paper.

  • For which season are they suited?

Not so important when you live in a temperate climate. But when you do not, it’s really important to remember that a leather sole is not really handy when you want to wear them in the autumn when every day is a rainy day (when leather is wet it gets soft and will wear out faster). So keep that in mind when buying shoes. Oh and by the way, a lot of people are afraid of suede. You probably think that suede is really delicate, nothing could be further from the truth. Suede can really take a beating and when properly impregnated against water they are better in the rain and snow than smooth leather. So don’t be afraid and embrace suede leather, they are really nice. Just look at pictures of Fred Astaire, he sure loved his suede.   

I should have learned much sooner, but I only recently read the wise words of Michael Alden from the London Lounge:  

“Never buy shoes that are too short. Shoes stretch in the width but never in the length.

Be careful buying bargain shoes at sales or outlet stores. They are never a bargain if they do not fit. 

It’s just like clothes. You are better off to pay much more and have a few pairs that fit and look beautifully than a closet full that you never will wear (and that cost you a fortune in effect).

It’s just like clothes. Go to a good tailor. Pay the full price. Get top service. Buy a few suits that are right. Do not fill up your closet with junk from bargain basement imposters. (A waste of breath all of this, but there you have it ..ONCE AGAIN.)”


I made a lot of mistakes. I acted too fast. Most of my shoes are pretty good buys when you look at styling, yet the fit is just plain wrong. I must conclude that I have really strange feet, and it’s hard to buy really great fitting shoes (except the Cavendish, they fit great). My dream is to own real bespoke shoes because I think that that’s one way of get great fitting shoes. Sadly, that comes with a price tag of over 2000 euro’s. I’m not ready to spend that kind of money on a single pair of shoes. I also don’t own a lot of shoes, and I did not try every shoe that’s out there. My next big shoe investment would be an Alden penny loafer in No. 8 (burgundy) cordovan…if the fit is alright. What do you think I should try? Let me know!

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