Really enjoyed this thread and agree with most of it that certain things such as an air of confidence / hood hair etc help. Two examples spring to mind.
The first was a woman (and her husband&daughter) in the shops. They clearly spent a lot or money, clothes looked very expensive ), yet it didn't look at all chic (which is what I think we are also referring to on this thread with the likes of Olivia Palmero ). The main issues were that the woman (very tall/slim/groomed) was on really tall heels which gave her a silly totter, she also had clearly had a fair bit of work (despite only being I'd guess in her 30s), huge lips & botox- made her look very cheap. The other thing, is that they were just at the shops- there is an element of trying too hard/ being over dressed that cheapens a look.
In contrast, just before Christmas there was a woman in the theatre who looked amazing and chic/wealthy. I'd say she was early 60s, she was probably size 16/18 but wonderful figure and (because not mega slim) had amazing skin. Her hair was grey and cut just below the ear but looked full, soft and (despite the fact it was blowing a gale outside), not a hair was out of place. Can't remember exact clothes details (which I guess is impression I would want- remember person not the clothes) but she had really tactile sort of clothes, trousers were velour (or something) and blouse was silk patterned- all in gorgeous jewel tones that really complimented her.
Personally, I like a timeless, classic look but rarely wear it myself as I prefer to have something a bit more funky/playful thrown in the mix. Plus with kids on tow, I very rarely exude an air of calm. PLUS I rarely get out minus kids so when I get to local pub etc I'm guilty of over dressing as it's my only chance!
As others have said, those I do know who have ££££, I would never guess by looking at their clothes. I think it is perhaps a lower middle class think to want to look more 'expensive' (I don't mean this in a snotty way, I'm from a very much working class background myself).
PS- have really enjoyed this thread.