I ended up leaving them at work last night then having a chat with him. It went like this:
Me: What would you say if I found a really fantastic pair of boots today?
DH: How much are they gonna cost me?
Me: Hang on, what if I told you I found a fantastic pair of boots today but they are red?
DH: What is wrong with the red boots I bought you???!!! You haven't worn them!
Me: Yes I know and I plan to but I really like these other boots and they are so stylish plus I can wear them with skirts cause they are tall boots - those red ones you bought me are lovely but they are just ankle ones. I will wear them tho.
DH: Ok, so again, how much are they gonna cost me?
Me: $260.
DH: Oh, that is a great price - I thought you were looking at ones that were $500!
Me: I was, but these are a really good compromise and exactly what I want.
DH: Ok, so buy them - some women have 20-30 pairs of shoes for work. How many do you have? 5??
Me: Sweet, Ill pop out and get them tomorrow.
LOLOLOL! I am wearing them now and OMG, they are so comfy.