Orange pants, orange pants, what do I wear with orange pants? Well, apparently, the last time I wore them, I did it with a gray button front, a belt, and mah boots. These poor boots are already falling apart, which is tragic; I’ve only had them for one season, but I wore the crap out of them last year. I think at some point in my future, I’m going to invest in a nice pair of boots. Still, for as cheap as these were, I got a really good feel for what I want in my next pair: leather uppers(instead of suede), the same mid-calf length, and a slightly higher heel than these (these have like a 1/2″ heel, and I’d prefer a full 1″, maybe even 1-3/4″).
I think that is one of the beauties of thrift stores and places like payless. If you’re buying something for the very first time, you can assess whether or not they will work for you, or what particular combination of characteristics makes it work for you.
Try all the things! For really cheap! And then invest! Sounds perfectly reasonable to me.