Over the last number of years, as I've spent less and less time going places in a car, and more and more time going places by walking or riding a bike, shoes have become a totally different kind of issue for me. If you mostly get around by car, shoes can just be something to keep your feet more-or-less covered. They don't have to be particularly water-proof, they don't have to be all that durable, or fit perfectly well, because you just aren't putting that much stress on them and you aren't getting them very wet or wearing on them much in the distances you're walking.
But being out in the weather and spending a lot of time walking and riding, it wasn't long before I discovered that, in Portland's year-round rainy climate, cloth sneakers are not going to cut it. You end up soaking wet right quick. Besides that, cheap sneakers wear out quickly if you're wearing them everyday and getting them wet and walking some distance on them. They also don't support your feet very well, and they become uncomfortable quickly, your feet get sore, and it's just a bad situation all around.
Finally, we decided to get me some leather boots from Aldo for riding during the winters. This was a big step up, but we still compromised and got cheap ones, and they only lasted me a year before they had holes and were leaking. Because of the cheap construction, there was really no way to repair them, and they basically just had to be thrown away.
The next time we upgraded a bit, and got some slightly sturdier boots from Rocket Dog, but still compromised on price, and while these ones lasted me about 2 years, twice as long, they had the same problem with the construction of the boot, which meant again that they were essentially unable to be repaired, and had to just be thrown out.
Finally, we decided we were not going to make the same mistake. We were going to get some boots that were both made well enough that, with some regular care, would last many years, and also ones that were constructed in such a way that the insoles and outer soles could be repaired or replaced if they were to wear out eventually.
We looked at a few brands, and I wound up with a pair of Frye boots (pictured at the top). They cost more than twice as much as the Rocket Dog boots. However, they already feel worlds apart. The leather is better quality, and they are more waterproof. They feel exceptionally solid, they are extremely comfortable, and they fit very nicely. They look and feel really great - you can tell that they were made with good materials, and with some care. They are also constructed in such a way that if parts wear out, they can be repaired or replaced.
So, I won't have to replace the boots for many years.
Which means that, over their lifetime, they probably will be considerably cheaper than buying a pair of Rocket Dog boots every two years. They will wear well, and develop a nice patina of use, and if parts of them wear out, they can be repaired for considerably less than the price of new boots. And, in the meantime, they feel much sturdier and more comfortable.
Well worth the extra investment up front, I'd say.