I think you've had some good pointers OP, but would say a lot of the 'detail' if you like will depend on where you live.
I probably fit into that style bracket, although I couldn't care less if anyone thinks my Michael Kors handbag is for secretaries or my Miu Miu a bit Eurotrash
That said, it is undoubtedly an easier look to do cheaply if you're reasonably slim and not too curvy. I am small and large of boob, so I tend to find myself spending a lot more on jackets and jeans as I can't 'get away with' some of the cheaper brands my leggier friends can pull off. (For the same reason, I won't be sporting the ubiquitous cross body bag any time soon. I guess what I'm saying is, 'take what works, ditch the rest and add your own twist).
Yes to pearls, simple diamond studs and understated jewellery. Up here, understated but unusual items in silver or enamel are quite popular (think local jewellery designer pieces rather than high street).
For cashmere, I favour Jaeger which is cheaper than Brora (although not cheap), washes well and often available on BrandAlley. (BrandAlley also good for high end branded jeans).
Minimal make-up, but a good non-clumping mascara and a decent base or tinted moisturiser. (I am still searching for the latter as I'm also very pale).
Not sure about the where to go query, but since you asked gastropubs are popular where I live, real ale and craft gins. Cocktails yes, but think classic or prohibition era, rather than sex on the beach.
If you really want to be up to date with what 'we' are supposed to like
, the Sunday Times supplements will do the trick.