What is the most money you would spend on an item of clothing?

All depends on what my budget is. If I'm stupid rich and it's no object what I spend? Whatever, if I like something enough and it looks good on me.

I really can't see spending ~thousands~ on any piece of clothing though, even if I had it to burn.

Several hundred, sure -- any good men's suit is going to run AT LEAST US$300 and that's a cheap one, just for example. But if I drop that kind of cash, it had better be something I'm going to get a LOT of wear out of, and it had better look good.

Have at it.