Thanks for all the input so far. I know that this $85 isn't the end of the world, it's just the most recent example. I want to be frugal and save more but there's always something that comes up, and this time it happened to be jeans. I wanted to save money and get a cheaper pair, but I know sometimes buying the more expensive better one is actually the right call, and there's no sense in buying pants I won't like. I think next time I'll take some more time before taking the tags off to make sure I really wanted it and it's the right fit and everything. Finding the right balance between taking care of my present self and saving for my future self is always a bit of a challenge for me, but I'm slowly figuring it out.
This is very true. If paying twice as much means an item lasts more than twice as long, or works more than twice as well, that can be a good call.
It's when you hit the point of diminishing returns that getting the "better one" turns into a bad deal. And that's different for everything and everyone. For a schlub like me, I don't care at all what kind of mattress I sleep on, so a $200 mattress is as good as a $2000 mattress and getting the fancy one would be a waste. But for someone with back issues, cheaping out there would probably be a mistake. For a casual hobby photographer, a $500 camera might do the job significantly better than a $100 camera, and a $1000 camera wouldn't provide enough marginal utility to make sense. But for a pro photographer, a $3000 camera can be worth it over a $1000 camera.
My current jeans have survived about two years on 90% daily wear, and about 40% daily wear for a year before that. They're nearly worn out now and will have to be replaced as they're my last pair. Luckily they were $5 from the thrift store so their price per wear is about a penny. I'm also a common size and a 25 year old dude with no fashion sense (and a girlfriend that is willing to go to the thrift store with me once every few years so I don't embarrass myself), so I think it's appropriate. Clearly this approach is not for everyone.
My point: you have to know what "matters" to you, whether from a utilitarian perspective or simply preferences. Too many people just like "nice things" and get the "nice" version of everything in their life without regard for what actually matters to them. My household has thousands in computer and camera gear (my GF is the pro photographer and I'm the computer gearhead that keeps her stuff running), three chest freezers, and multiple raw-fed Australian Shepherds, but we also have a single cheap car (high-miles 2009 Hyundai), a much cheaper house than everyone I work with, healthy home cooked meals every day, and yes, thrift store clothes.