I know a guy who buys most of his shoes at estate sales. He lives in a town with a lot of wealthy people. He buys $1200 shoes for $5. Always in pristine condition. Often never worn. Current or classic styles.
Wow thrifty guy! FWIW, my wife gets most of her and the kids clothes at salvation army. She is good at that - I do a terrible job. Went in and got kids pants and then she asked “Did you have them try them on?”. Whoops.