The biggest correlation is between upfront expense and long-term durability. Good shoes can be resoled, which is fairly cheap and can be done quickly. A good pa

The biggest correlation is between upfront expense and long-term durability. Good shoes can be resoled, which is fairly cheap and can be done quickly. A good pair of leather shoes could last you 10 years. All you'd have to do is get them resoled each year or however often you wear through them. Flip flops don't provide a lot of ankle support, and for some people that can be an issue. I walk between 5-7 miles a day, and while I find flip flops comfortable for lounging around, I wouldn't want to walk any serious distance in them. I've found that certain shoes are much more comfortable than others, and they tend to not be on the cheap end of things (not the most expensive either). Because of how much I walk, I'd go through several shoes a year, and now I'm switching to only buying shoes that can be resoled. It will save me a lot of money in the long term.