My current shoes, a 2009 christmas present from julia that I've liked and worn daily since, are starting to wear out. Which has me thinking about shoes, and because I'm cheap, cheap shoes. I've previously worn shoes that cost about $40 and last about two years. Spending $20/year on shoes isn't so bad, but if I can do better I would like to. After looking around r/Frugal it looks like there are a lot of people who think it makes sense to buy more expensive shoes that would last longer. Several suggest buying leather shoes in the $100-$200 range, taking good care of them, and resoling them as needed. They would need to last 5-10 years to come out even, though. And resoling might be $20? If they needed yearly resolings I'd not come out ahead.

I've also been walking more lately, mostly because I now live closer to work [1] and can walk there. (3.1 miles round trip) Since my shoes tend to wear out because of wear proportional to distance (as opposed to my other clothing which wears out because of wear proportional mostly to the number of washings), if I can reduce the number of miles I walk in my shoes they should last longer. So I'm going to try to build up to commuting barefoot. Which, as long as you walk properly [2] and avoid glass and things is supposed to be better for you.

[1] It also took noticing that it was cheaper to go from a monthly pass to putting money on my charlie card. And once I'm saving $2.50 every day I walk, I find I end up walking a lot.

[2] Toe down first instead of heel striking.