I've acquired some wealth, and can easily spend a (few) grand or more on clothes (and regularly do so). The more your investments throw off, the easier it gets

I've acquired some wealth, and can easily spend a (few) grand or more on clothes (and regularly do so). The more your investments throw off, the easier it gets to spend (or waste) significant money. What is more money in the bank worth, past a certain point? If you're worth $5M, and you make 10% a year on that, what do you do with $500k per year? Second, I agree on the 2 points you brought up; 1) can I afford it?, and 2) do I want to spend money on this? But the more you have, the less it matters. Forget retirement. If you enjoy skiing, why wouldn't you buy a pair of excellent ski boots? Luxury items can be awesome.