VIII. Shoes

One of my father's rules is to always take care of your feet. Keep them clean, dry, comfortable, and free of injury. My preferences for dress shoes are all derived from that simple axiom. No matter what, always pick your dress shoes on how they feel, how long you can wear them comfortably, and how far you can walk in them. Every other consideration, no matter the aesthetics, is secondary. You will hate wearing a suit less if your feet don't hurt at the end of the day.

A good personal example is the time I decided to walk to work in a new pair of shoes. I decided to upgrade to a “quality” leather shoe, and it seemed comfortable enough walking around the apartment. I lived close enough to walk to work at the Pentagon in those days. It was less than a mile, but by the time I passed through the front door my ankles had bled through my socks. My only saving grace is that the Pentagon is also part shopping mall, so I was able to acquire bandages to shore up my ankles for the rest of the day. As an aside, there's a DMV in there that was the most efficient I've ever experienced, and the barber is great if you want a cheap, fast haircut in a single style. The point is the shoes looked okay until I fully tried them out, and no amount of modification after the fact mitigated the bleeding.

I now only purchase “comfortable” shoes. You're probably not going to patronize a cobbler for custom shoes, they just don’t exist anymore. Instead, you should find a retailer that generally provides styles and fits that work well for you, and that may take trial and error.

Colors

I've heard the axiom that your belt color and your shoe color should match. There's likely some truth to it, because the same general coloring rules apply: wear black with a darker suit and brown with a lighter suit. If your closet only contains two shoe colors, black and brown will do the job for both formal and informal occasions. Other colors are also acceptable. I have one pair of dark blue shoes that work well with a variety of different outfits. Another pair is primarily brown but with a white sole to provide contrast. I wouldn't recommend fully white because you'll just be polishing it constantly with all the dirt and grime in the city.

Material

Absent ethical objections, your quality dress shoes are likely going to be leather. Your only other options are some kind of plastic (not great) or some form of canvas that may lack formality. Within leather, you have multiple sub-options. There is the basic smooth leather that is most common, patent leather that is so processed it has a glossy finish, and suede for a more matte and informal finish. I would always avoid patent leather unless the dress code explicitly requires it. My blue shoes above are suede and provide some diversification. Note that you will have to treat suede to ensure it’s waterproof.

Structure

How the shoes are constructed is the most important aspect for comfort and wearability. A poorly constructed or misstructured shoe will make you miserable. You will have to do extensive testing to know what works. I'd recommend dedicating an afternoon to trying a host of options with a knowledgeable shoe monger.

Toe Box. The toe box is the front of the shoe where your toes live. For some reason, the toe box on many traditional dress shoes is substantially larger than required in a boxy or elongated point; compare the shape of the dress shoe to a running shoe. I recommend a toe box that actually fits your foot properly. That extra space will not be comfortable and it will hinder your ability to walk. The worst is when the long toe box forms a crease that pinches your toes. Sacrifice aesthetics for practicality and choose a shoe shaped like a human foot.

Heel. Heeled shoes on men are an anachronism from horse riding and are, therefore, a preference. Mine is to not include heels. I find the slight elevation change from raising the heel alters my gait in a way that isn't comfortable, putting more pressure on the front and toes.

Support. My second reason for not joining the military is that my feet are flat. My solution is to replace the insoles with much more supportive inserts. They’re the difference between no pain and being crippled after a long walk. You may be paying an extra $50–75, but a supportive shoe is vital to both your and its longevity.

Laces. The laces that come stock with dress shoes are usually awful for staying tied. It seems you can't walk more than 15 feet without them coming undone. Don't be afraid to remove those less than useful laces and replace them with something better, made of either leather or canvas rather than plastic.

Socks

I had a roommate who rarely wore socks because “you don't wear socks with boat shoes.” Please don't be one of those guys who wears dress shoes without socks. You're putting bare skin in a leather case with marginal breathability. That environment is a breeding ground for all kinds of microorganisms that will make you to stink and increase the risk of foot infection.

Men’s socks have undergone a Renaissance. The sock drawer is no longer a monochromatic black and gray.  You can find them in myriad styles and colors to express your individuality, at least when you're exposing your ankles like a saucy Victorian. Still, the solid colors are easy to pair without having to think about it, and they make laundry easier if they’re all the same. Another consideration is that many dress socks are quite thin. I prefer a more robust sock because it helps keep the moisture at bay and provides a little extra cushion. No matter what you wear, be sure to take the socks that you will be wearing to the fitting.

Other Kinds of Shoes

We've only been talking about traditional men's formal shoes in this chapter, but they're not the only ones you'll see. They are, however, the only ones I recommend in a professional environment. Just because some tech CEO wears sneakers and a blazer doesn't mean the combination looks good. Cowboy boots are a cultural and political signal. Sandals would be humorously out of place anywhere but an album cover.