A Man's Guide to Boots and Shoes


Over 70 years ago, archeologist Luther Cressman discovered perhaps the world’s oldest footwear in Central Oregon. The sandals were dated to be 10,000 years old, and from the pictures I’ve seen, were made with intricate weaves that indicated they were not only functional, but also stylish in design. From our tribal days to modern times, men have searched for and valued footwear that both looked good and got the job done.

The goal of this article is to give you an overview of a man’s options when it comes to footwear. I’m not going to try to sell the idea that you need a pair of shoes for every occasion, but I would like to expose you to the concept that quality footwear that fits well is a worthy investment, and that the right shoes for the right situation can substantially elevate your personal style and comfort.

Why care about your shoes?

A man should care about his footwear if for no other reason than the fact that it constitutes the very foundation he stands upon. In an average day, you’ll ask your shoes to absorb the force of your weight 3000+ times; a poor choice here can lead to not only discomfort but injury one step at a time, especially if you select shoes that inhibit your body’s natural gait and cushioning system.

Then there is the appearance aspect. Separate from the rest of your clothing, shoes are a visual endpoint and receive a disproportional amount of attention; despite covering only 5% of your body they can make-up more than 30% of the visual judgement we make when sizing up a stranger.

Ideally you want to choose footwear that is both functional and stylish – by following these footwear selection principles this goal can be easily achieved.

Four Footwear Rules

1st – Wear the right shoe for the occasion – this is the most common mistake I see men make when it comes to footwear. Running shoes have a purpose; they protect your feet while running. Steel toe work boots have a purpose; they protect your feet while working. And wearing these shoes outside their prescribed function is fine as long as they are still appropriate; however, many of us take this to an extreme and have abandoned the middle ground between formal and ultra-casual.

2nd – Invest in quality – Not every man can afford to spend hundreds of dollars on his shoes; however, many of those who can instead choose to waste money elsewhere and buy new inferior shoes every few years. This is never a winning strategy, as low quality footwear is held together with glue and made with cheap raw materials such as cardboard and paper that does not age well. You can save money in the long term by buying more expensive shoes that last for decades.

I want to expand on this point just a bit more; to buy quality, many men will have to save and budget for the purchase. This isn’t a bad thing – in fact, it can instill a respect for the quality of the product and encourage you to take better care of them when purchased.

And don’t forget the thrifting option. Assuming you can find a pair of quality shoes that fit you from Allen Edmonds, Alden, or another manufacturer, you can send them back and take advantage of their re-crafting and re-soling service. A new pair of shoes for a fraction of the cost, rebuilt to serve you for 20 years.

3rd – Never sacrifice proper fit and comfort – buy the right shoe size, even if this means paying a bit more and purchasing your shoes at a brick and mortar shop vs. going the tax free/lowest price online route. Actually, this isn’t a bad deal, especially if you support a local small business that can really give you solid guidance as to what styles are available and show you how to take care of your purchase.

Use a Brannock device to measure your foot if you’re not sure about your size.

Another fit issue is paying attention to shoe width. Men with extremely wide or narrow feet learn about this from an early age, but many men who would be better served by just a slightly wider or narrow shoe never discover their perfect size because the normal sizes do an OK job. I challenge you to take the time to find the right size…’d be surprised about what you’ve been missing, especially if you spend quite a bit of time on your feet. Look for variations in arch support and toe structure as well.

4th – Take care of your shoes – We’ve written about this extensively here at the Art of Manliness. Learn how to waterproof your shoes in this classic article and then learn how to shine your shoes here.

In addition, rotate through a few pairs to allow them to dry between wearing and ALWAYS use wood shoe trees that will quickly soak up perspiration. This is especially important for leather shoes, as the interior of a dress shoe has often not gone through the harsh chemical treatment of the upper and is more susceptible to rot.

Common Footwear Terminology

  1. Sole – This is commonly referred to as the bottom part of the shoe or boot and can be further divided into the outer sole, mid-sole, and insole depending on the type and quality of the shoe being discussed.
  2. Upper – A general term that refers to the part of the shoe above the sole.
  3. Brogueing – a form of ornamentation in which tiny holes are carved into the shoe’s leather. An important point to remember is that the more decoration on a shoe the less formal it becomes.
  4. Open Lacing – One of the two lacing systems used in oxford shoes, the open lacing system delineates the shoe in question to be a blucher. The shoe’s tongue and vamp (parts of the upper that cover the top of the foot) are cut in one piece with an open throat.
  5. Insole – As mentioned above, a subsection of the general term sole, the inner sole is the layer of the sole upon which the foot rests. A quality insole can mean the difference between a shoe that will last 5 years and one that will last 25.
  6. Heel – The back portion of the shoe that comes into direct contact with the ground and gives elevation to the foot when the shoe is worn. Heels are often built from 2 to 4 pieces of leather called lifts and reinforced with rubber or metal.
  7. Laces – The choice is usually round or ribbon, with round having the advantage of being stronger and more formal thanks to their core while ribbon laces come in a variety of colors and are more elastic and are thus a good choice for athletic shoes or hiking boots.

Men’s Footwear Type Overview

Dress Shoes

Oxfords are lace-up shoes built to be worn below a man’s ankle. They are commonly divided into balmorals and bluchers due to the difference in their lacing systems. Balmorals are commonly referred to simply as “oxfords,” while bluchers are referred to as derbys but rarely oxfords; all of this leads to confusion naturally. So for simplicity’s sake, I will refer to balmorals as balmoral oxfords and bluchers as bluchers.

Balmoral oxfords use a closed lacing system and are normally styled more simply than bluchers. Thus balmoral oxfords are classified as the dressier of the two; they are best worn with suits and formal wear. I advise every man to own a classic pair of balmoral oxfords to wear with his 2-piece suit.

Read the rest of the article