I've been obsessed with clothes as long as I can remember. As a teen and up to early 20s it was all hippy dippy long Indian dresses and Laura Ashley. I stopped wearing jeans in 1990 and never really wore tailored trousers.
I went through an incredibly dull and conservative period when I first started work and bought neat little suits initially from Wallis, then Alexon, Windsmoor, Kaliko, Jaeger for work but non work was still all droopy Laura Ashley (which I've still got a soft spot for although the quality of Laura Ashley went into serious decline) That was followed from mid 30s to mid 40s by an equally conservative Hobbs period.
In 1998 I discovered a shop in Amsterdam selling really quirky, highly tailored clothes (some of which came with instructions) which were like nothing I could buy in the UK. I used to go to Amsterdam about every 18 -24 months to stock up on work clothes. Last purchase was in 2017. I've still got loads of it, although much doesn't fit and it's more tailored and structured than I wear now.
In 2000 Lulu Benson and Janey Dalrymple opened Arkangel in Edinburgh and Helen Bateman opened her shoe shop. Jane Forbes opened Frontiers in 1990 but moved to its present location in 2007. Arkangel stocked mainly eccentric French brands (Lillith for example- the current iteration of Lillith is a far more "don't scare the horses" look than its earlier version) and Helen Bateman's shoes were her own designs which didn't look much like what was on the high street. Unfortunately Arkangel and Helen Bateman have closed ( not through lack of customers, the owners had simply had their time in the rag trade) I still have loads of stuff from Arkangel (hope springs eternal that I might fit into them again)
Frontiers is still going strong. I found brands like Samantha Sung, Edina Ronay, Baum und Pferdgarten, Ganni, Rixo, &Daughter, LF Markey, YMC, NRBY and Pazuki there. There's been a small amount of original 1950s and 1960s clothes mixed in with this.
Of course all of these shops and designers follow trends to some extent but their clothes aren't intended to last only 1 or 2 seasons. I don't think I've ever thrown any of it out because it was out of fashion- some I've had to because I've admitted it will never fit again.
I've always disliked clunky shoes/ block heels/ platform soles. I don't care how unfashionable ballet pumps or low heeled stilettos/ kitten heels or flat boots are, that's what I'm sticking with.
I sort of love Doc Martens because even although I never managed to break in my one and only pair of Docs, Docs and similar to Docs, have never been out of fashion.