I have some lovely bags and shoes, one bag was thousands (a gift but I'd have saved up if not) and several shoes in the hundreds. My day to day bag is a Louis Neverful in the brown check which the last time I looked was over £1k and is very recognisable, but I have toddler twins and it holds double bottles, nappies, snacks, and all the extra junk I need to ferry about. I've had it years and it's my carry on flight bag and beach bag too. I don't really care if people think I'm carrying it for status.
Some of my things are recognisable brands, some aren't. I have them all because I like them. I also have cheap stuff, which I bought because I liked too.
My Chanel stuff has rocketed in price, and I'll give to DD in the future.
I think with the more expensive stuff, I get a greater sense of pleasure, but that comes from within. E.g. I have a pair of rockstuds I got years ago, which I bought when I did so well at work, I got an unexpected bonus. So I smile when I see them because I associate them with self achievement. Don't wear them much anymore, but I just like to see them now and again, and think "yeah, I did that."