It depends. For someone who doesn't wear "formal" clothes often, but enjoys clothes nonetheless, you can get away with a couple suits and a few sport coats/pants. While I agree you need to be some stage of well-off, many here see clothing as a hobby and take enjoyment from the process of learning, seeking and experimenting. While there are some that order bespoke as a matter of course, they are likely not interested in clothes on our level: Rather, that is just simply how they've always lived, only wearing custom clothes because that's all they know. Like anything else, if you plan on expenditures and map your resources (income, time, etc) around them, you should be able to enjoy bespoke clothing without eating Ramen every night. That said, if you ever find yourself questioning if you have enough, you don't. In terms of vanity: it's not that I'm vain, it's just that I'm better than everyone else.