GARMENT ONE

Leather Shoes

Cheap shoes look cheap even when they’re new, but good shoes look good even when they’re old. — G. Bruce Boyer

As the foundation of any outfit, shoes can teach you a lot about how to acquire and care for your entire wardrobe. A few pairs of good­-quality all-­leather shoes will last for years, if not decades; harmonize with a wide range of outfits and activities; and be a vehicle for learning about wardrobe maintenance. But I’ll be honest: building a shoe collection is hard work because of all the options and makers. Before I get into all that, though, let me explain the types of shoes I’m talking about.

By the 1930s, the styles I suggest in this chapter — oxfords, derbies, monks, and loafers — had all been well established. Standard pairs look almost identical to what is being sold today, except for subtle things like silhouette and decoration. And those change mostly from maker to maker, not so much over time. Perhaps because they are so useful while not extreme in design, classic leather shoes seem to escape the fluctuations of fashion unlike any other garment. That alone makes them well worth an investment.

Quality

Before we get down to the nuts and bolts of leather shoes, the overarching argument is that you need to invest in quality. This is much easier said than done. Most of us have grown accustomed — and not just with shoes — to poor quality. There has been a rush to the bottom in the mass­market footwear industry, and most customers are unaware of how flimsy and poorly made their shoes are until the shoes start to fall apart after a short time. Even then, we are so used to it, and the shoes are so cheap, that we just buy another pair. And over time we spend a fair amount of money topping up landfills and unknowingly promoting poor working conditions.

Consider, first, the materials that go into a shoe. Various types of leather are used for different purposes: the upper, the sole, the internal structure, the lining. Other materials — cork, metal, and thread — also form the structure of the shoe. Many of these are never seen by the customer, so it is easy for manufacturers to replace them with lesser-­quality items, but some makers do not compromise. Quality makers source the best leathers they can, from the finest tanneries. Then they use some hand labour along with highly skilled mechanical techniques to construct the shoes. They do all this because they want to make shoes that are not only durable but also comfortable and stylish. Most of all, these shoes are imbued with their creative vision, in the silhouette and finishing.

If a maker is going to take the high road and do everything to the best of their ability, there is a cost associated. Cost usually, although not always, corresponds to quality. And a minimum exists, below which quality just can’t be found because of the fundamental costs of materials, design, and construction.

As a customer, how can you know whether that is the reason for a high price tag? Truth is, it’s up to you to do the research. Ask the seller plenty of questions and find out what you can about the maker. What I’ve learned to look for is a shoemaker who is transparent about where their shoes are made, what processes they use, and which tanneries they source their leathers from. This often means, in my experience, smaller European brands or heritage makers.

As hard as it may be to believe, investing in quality can actually save you money. Here’s my experience. A number of years ago I bought a pair of shoes for around $100. They had low-­quality leather uppers, a synthetic liner, and glued-­on rubber soles. No matter how much I took care of the uppers, they never took a polish well, and the shoes lost what little shape they had in just a few months. After a year the lining started to fray and come apart. After two years the soles began to wear thin and could not be replaced. There was nothing I could do but reluctantly throw them away.

On the other hand, I have a pair of mid­quality shoes that cost around $500. They are made completely of leather that, while not the highest grade, is of good quality. The front half of the sole has been replaced once (for a cost of around $50), and they are now almost ten years old. If, in the next ten years, I were to have them completely re­-soled for approximately $200, that would put their per-­year cost at $37.50. The cheaper shoes? More, at $50 a year. And, of course, along the way the more expensive shoes look and feel much, much better. In a sense, you are pro­-rating the cost of your shoes: it isn’t about the upfront cost, but how that cost is spread out over the life of the shoes. Longer life, lower year-­by-­year cost — not to mention, a better experience over that time of both fit and style.

Consider, as well, the added environmental benefit: since I’m not throwing the shoes away and replacing them every year or so, I’m producing much less waste over the lifetime of the shoes. So the first lesson is not so much about shoes but about spending. You can change your habits from a lot of small purchases to fewer, larger purchases.

But investing in quality is also about appreciating good things. Yes, that includes exceptional craft and materials that will give you a feeling of satisfaction every time you wear the items. For me, however, quality is also about beauty. There is something so unique, so beautiful, about how fine shoes are able to combine function and aesthetics. Having something in your life that is aesthetically beautiful — which could be because of the leather, the shape of the shoe, the details in the finishing, or all three — nourishes you in ways I think we undervalue. If the world around us is full of ugly things, we can’t help but feel that the world itself is ugly. Fill our lives with beautiful things, and we believe the world is just that much more beautiful. Neither is a completely true reflection of reality, of course, but I prefer to choose positivity over negativity.

What Makes a Shoe a Shoe

When I grew up, like many people I called leather shoes “dress shoes.” Partially this is because I only wore my leather shoes to church, with my ill­fitting polyester suit (vivid detail about that in the “Two-­Piece Suits” section). It was also because we as a society don’t really know what “dress” is anymore. Technically and historically, a “dress shoe” is any footwear you wear with black or white tie, such as patent leather oxfords or opera slippers. What I’m talking about in this chapter is any style of all-­leather shoe meant to be worn with anything — anything except formal dress on one end and for playing sports on the other. Within that range, however, are a multitude of options. But before we look at the outside, the style of a shoe, we need to start with the inside, what makes a shoe a shoe. And that begins with the last.

LASTS
Typically made of wood or plastic, a last looks like a foot without toes and is the shape around which leather is stretched to give the shoe its shape and silhouette (not to be confused with shoe trees, which help maintain shoes in good condition, see “Caring for Your Wardrobe”). All shoes made of leather are constructed on lasts, which are mass produced at standard sizes. Lasts can also be custom­ made and shaped, based on your measurements, for custom shoes. A mass-­market or custom last can be rounded or pointy toed, and the way the shoe will shape around the instep, the volume of the shoe, and even the shape of the heel are determined by the last.

Understanding lasts will liberate you from the shackles of shoe sizes. I grew up thinking my shoe size was 10.5 wide. It turns out, the situation is more complicated than that. First of all, my left foot is slightly longer than my right (for the vast majority of people, one foot is a different size than the other). However, my right foot splays more than my left when walking. So which one is really bigger? I also have a high instep (the part of your foot right under the laces). All of this means that I used to buy shoes that were too big, trying to compensate for all my idiosyncrasies, so that they would feel “comfortable.” This really meant I was striving to not feel the shoes at all. The lasts that all those poor-­quality shoes were built upon were generous: wide and voluminous. Even though they measured 10.5 inches long, the space inside the shoe was enough to accommodate a range of foot sizes, from medium to wide width. Which meant they fit most people badly and fit no one perfectly.

Then I discovered not only that shoes are built on lasts but also that lasts come in so many shapes, depending on the maker. And I realized that if I found the right maker using just the right shaped last for me, I could have the length I needed plus the height in my instep, but in a shoe that hugged my ankles and held my toes firm. However, finding the right last means trying a variety of shoes from a variety of makers. But honestly, that is part of the fun. With every shoe you try on, you learn more about yourself and about shoes.