Reddit mentions of Corcoran Jump Boots (Black, 12 1/2 EEE)

This is an interesting BIFL subject. There are actually arguments to be made both ways on this. It is possible to find BIFL boots, but whether they actually last that long is heavily contingent on how you use them. As an 8-year Army vet with two years spent on deployment, I have spent a lot of time in boots. On the one hand, I still have the pair of Corcoran airborne jump boots I bought in 1987. They're shiny dress boots, though, so they're not for everyday wear. I also have one pair of boots from the original two pairs I was issued in basic training in '87. They're soft as bedroom slippers at this point, but the soles are worn thin and treadless. I have several pairs of various boots I bought or was issued after that, and their condition varies. The one thing I had driven home to me in Afghanistan was that while a pair of good quality boots will easily last for years, they will start to lose "effectiveness" pretty quickly. When I was drag-assing up and down every ridge and valley in Paktia with a bunch of infantry guys, I found that the "comfort level" of a new pair of boots degraded to about 50% well inside a year. Even changing the insoles didn't really matter. They simply got stretched out and the soles degraded and became less cushioned. They'd stay at around 50% comfort essentially forever thereafter, but I decided a couple hundred bucks a year on new boots was worth it.

The thing about boots nowadays is that they're a lot more varied than they used to be. Once upon a time, when you bought boots you got weighty, thick black leather monsters with heavy soles that took months to break in, like the WW2 era design Corcoran jump boots I bought in '87. Boots like that are definitely BIFL, but as far as confort, they leave a lot to be desired. In the last 20 years though, a lot of sneaker technology has found its way into boot design. Now even current-issue military boots are lightweight with polyurethane foam cushioning built into the soles and GoreTex lined breathable nylon uppers. My feet were a lot happier in modern 21st century boots than they were in the old black leather monsters from the 80's. New boots break in quickly, within hours. The drawback is that the light, comfortable boots simply don't last as long. I went through about five pairs of boots in the two years I was deployed to Afghanistan. Granted, that's extreme conditions walking miles every day on rough terrain.

So really, you're kinda stuck with a choice between heavy, acceptably comfortable monsters that'll last for decades, or light, phenomenally comfortable modern-tech boots that really only reasonably last a couple years of constant wear.