I think you are experiencing a period of unrest, if that makes sense. I've been there in the past, and whilst I never did the F&F thing I could never quite fit my tastes to my environment.
I don't like smart or city looks for me, but I grew tired of rainproofs and mountain style stuff after years of mooching around fells. I longed for a kind of laid back slouchy luxury, where the items were lovely quality and natural fibres but not particularly 'rich' if you see what I mean. So a sort of off duty dancer look with a slightly less frivolous hint of bohemia.
In reality I would end up in yoga type clothes or waterproofs 
These days I have less and less stuff, but all of it means something to me. I try to bridge the gap between practical and just plain lovely things, and to keep it to a minimum.
Look at what you reach for most each season.
Do you prefer tshirts, vests or dresses in summer?
There are different types of rural and city, too, not just one bland, homogenous look. The F&F look is very specific so only go there if this is super comfy to you.
I don't wear typical country togs because I find them a bit stiff and bulky for me (my old dubarry boots were like lugging around a lumps of concrete).
I tend to put my money on accessories, so a nice cashmere wrap, leather sandals and some good trainers for walking.
So what is your lifestyle and how do feel at your best if you blot out other people's perceptions of you? It pays to imagine this because it will save you time and money in the future. If you feel like fancy dress it isnt working. I felt like that in pretty dresses, even tho i suit them. It's unsustainable for both your pocket and the environment.
Find your own niche, your 'tribe' as it were, and if you feel overwhelmed socially to fit in, just add touches to it rather than slavishly following.