 What's the most amount you ever spent on a pair of shoes? The most I ever spent was, I think about 9,000 Travis Scott friends and family, the Purple Joints. What's the most you ever spent on a pair of shoes? Yikes. Alright, before trophy rooms even came out, I spent three bands on them. Now they're 15. Damn! I haven't said the best of them, I haven't said the best of them. What is the most you ever spent on a pair of shoes? I hate to say it, $2,000. Oh, what did you get? Trophy room ones, and they're at like $1,500 right now. You're not the first person that said this. The last person spent $3,000. That sucks.