 What's the most you ever spent on a pair of shoes? It's probably $9,000 on the Friends and Family Air Max. I just got my pair yesterday. Oh, really? Yes. I'm so happy. I'm so happy. What's the most you ever spent on a pair of shoes? Man, I dropped $500 on the off-white dunks. What's the most you ever spent on a pair of shoes? I'm trying to think. I don't know, honestly. I'm going to say $1,000 on some Chicago-wise.