I will spend decent money - but not silly money - on things that will get well used. And save where I can.
So while we do need sailing boots (DD sails with the sailing club, and is in a Sea Scout unit) - we tend to get them in places like Decathlon when we can as they are solid boots and work perfectly for the purpose. But if we can't get there when necessary (it is a couple of hours drive away from us - fine on occasion to do with other things locally there, but not just for 1 pair of boots in a hurry), we might need to order online (bit more expensive) or even get them in the local sailing shop (LOT more expensive). In fairness though, she will use them so much that she wears through them mostly, it's rare that she grows out of them.
The same with things like runners and hiking boots - they get well used, I will get decent pairs normally but not spend silly money on them (Mountain Warehouse boots are usually great - if I have time to order them as no shops locally to me).
But DD is very happy with plain green or navy basic wellies from Tesco or similar, and for the use they will get, I'm fine with that too.
And I know she does have a lot of footwear, but she uses them all thoroughly. And we can afford to send her to the various activities if we budget properly and make sensible savings (buying decent but not top quality gear that will last sufficiently well while she is growing, buying in sales, etc). But the activities are also significant for DD in helping her to manage her ADHD and ASD, and to learn social skills in a non-school setting. So I will sacrifice things I want to make sure she gets what she needs - as often times we have found that while paying for specific therapies may be somewhat useful, being careful about the types of other activities and letting the relevant leaders know her issues can actually be more helpful to her in learning to cope with the world around her and not mark her out as totally "different" to everyone else.
Meanwhile, as my feet stopped growing years ago, my local shoemaker knows me well from getting shoes and boots re-soled and re-heeled on multiple occasions! 