Oh, boots, I forgot about them! Yeah, tall boots are a sticking point for me. A) I have large feet, skinny ankles and wide calves and B) I'm a cheapskate so any item where the baseline cheapest price for a quality option is $100 is going to give me palpitations.
I also dislike categories of items I can rarely thrift, like boots and bras. (Well, you can thrift bras, but I gotta draw the line somewhere.) I feel like I balance out my costlier shoes, jeans, tops, with the ones that I can find cheaply secondhand, but (understandably) people keep decent boots until they fall apart, so they're rarely out there secondhand. Same with quality handbags but I'm not much of a fancy bag person so I don't really care.