What Terry Pratchett Taught Me About Expensive Boots

If you are checking out Stridewise for the first time, you might be on the cusp of graduating from boyhood (i.e., Vans, Converse, etc.) to something more befitting a gentleman.

Perhaps you have already come to appreciate the significance of a well-made pair of boots, but your imagination has not yet crossed that threshold where you can picture yourself in shoes that cost more than a car payment. Or maybe you have a pair (or three) of quality boots, but you can’t seem to get your mind off that new discovery. In any case, you are in the right place.

As with most guys, I was introduced to quality boots by Red Wing. I walked into the store thinking that I wanted a 6–Inch Classic Moc (which is a fine choice to be sure), but there was something about the Iron Ranger that I couldn’t quite put my finger on at the time but nonetheless captured my attention.

At first, the Iron Ranger did not seem like it worked with my casual — boyish, if you will — style, but there was a sophistication and heft to the shoe that was alluring. So after several stops into the Red Wing store, and even more visits to Stridewise, I ended up with a pair of Copper Rough and Tough Iron Rangers. To the extent that they were not my “style” at first, I found over time that they demanded more of me than a pair of Vans. And I liked it.

red wing iron ranger

Read the full Red Wing Iron Ranger review here!

Up until that point, the most I had ever spent on a pair of shoes was maybe $150. The idea of spending over $300 on one pair of boots felt almost wrong. That was about to change.

Over the next couple months (about the time it took to break in my Rangers), I discovered that there was a world of other boots out there — many of which cost in excess of $500. The quality and construction, and even the smell, of a well-made pair of boots was intoxicating to me. I would be lying if I said my wife didn’t roll her eyes more than once as I ogled a newly discovered brand online. After buying a pair of Alden 403s, my world changed. The idea of paying hundreds for boots didn’t feel wrong any longer — quite the contrary.

The reality is that for years I routinely paid $100 for shoes that would wear out and look shabby in less than six months. As I thought about this concept, I stumbled on what has become known as the Captain Samuel Vimes Boots Theory. It comes from a novel by Terry Pratchett, who was an English author and satirist, best known for his Discworld series of fantasy novels.

Alden Indy 403 street

The Alden Indy 403. Read why one contributor named Alden his favorite boot company.

The Boots Theory comes from a passage in his novel Men at Arms:

“The reason that the rich were so rich, Vimes reasoned, was because they managed to spend less money.

Take boots, for example. He earned thirty-eight dollars a month plus allowances. A really good pair of leather boots cost fifty dollars. But an affordable pair of boots, which were sort of OK for a season or two and then leaked like hell when the cardboard gave out, cost about ten dollars. Those were the kind of boots Vimes always bought, and wore until the soles were so thin that he could tell where he was in Ankh-Morpork on a foggy night by the feel of the cobbles.

But the thing was that good boots lasted for years and years. A man who could afford fifty dollars had a pair of boots that’d still be keeping his feet dry in ten years’ time, while the poor man who could only afford cheap boots would have spent a hundred dollars on boots in the same time and would still have wet feet.

This was the Captain Samuel Vimes’ ‘Boots’ theory of socioeconomic unfairness.”

Red Wing Iron Ranger finish

Now I’m not here to focus on economics or social dynamics, but I could identify with Captain Vimes wearing out his boots too often. In fact, my garage is lined with old — but not that old — shoes that are only good any longer for lawn mowing.

So could it be that buying that pair of high-quality boots (expensive as they are) is actually the responsible thing to do? I say yes! Just think about how many pairs of inexpensive shoes you have purchased over the past five years. If you’re like me, it shouldn’t be too hard; just go check the garage or the back of the closet.

Do the math, and you likely will be surprised.

Now, consider that a good pair of boots can last 10 years or more if taken care of properly. The Goodyear welt construction even allows you to resole them many times over, making it a truly lifetime type purchase in some cases. All the while, you have a pair of shoes that is supremely comfortable, develops character over time, and demands thoughtfulness in overall style. What’s not to like?

I suppose the prudence of this approach to footwear could be questionable if you develop an unhealthy obsession, but I’ll just leave that here!

If you’re new to the world of well-made boots, welcome. And whenever you end up taking the mental leap necessary to re-imagine the role of footwear in your world (if you haven’t already), Stridewise will be here to help navigate the path. In the meantime, hold your head high the next time you get that look from your wife as you admire your own feet, and let her know that you are saving money and looking like a gentleman in the process!

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Bryce Carlson

Bryce spent the early part of his career as a musician and pastor. Now he spends most of his time as a lawyer, husband, and dad. He lives in northern Colorado and enjoys all things fly-fishing, music, and fine wine. Bryce has three kids and is married to the best trainer and nutrition coach in Colorado.

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