My go-to cool weather jacket is a leather A-2 flight jacket I have been wearing for 30 years. But they tend to look better as they age.
I wear running shoes until they are literally falling apart. If I find a pair of shoes that are actually comfortable, I don’t let them go until they are unwearable.
I mostly wear T-shirts and jeans. I still have concert T-shirts from decades ago that I still wear.
My annual clothes budget is probably around $200. Some years, almost nothing. Some new socks and underwear, and that’s about it.