Hello and welcome Awks I'm relatively a newbie on here. I'm in my 40s and yes I did have that Bennetton rugby shirt complete with Argyll socks, penny loafers and turned up jeans.
My style story is nowhere near as precise a you guys. I've always been interested in clothes and used to read Cosmo, Vogue, Elle et al in my early teens. In the 6th form I dabbled a bit in the goth look, at uni I was a bit preppy, shopped at Benetton, was never into the grungy look. I bought a Gucci handbag, watch and Louis Vuitton handbag from my Saturday job money.
When I started work I wore Hobbs and dressed quite smartly but coordinated and matcha matchy, handbags same colour as shoes! I was dressing quite smartly when I met dh I was working in another country where the women dressed stylishly and I tried to emulate that.
Tbh fashion wise and my style went down badly when I had dc. I moved to a small town with small town shops and Next, M&S and Debenhams were the only shops on offer and that started my fashion decline. My wardrobe was woeful and I bought some horrors. When dc started school I wore the school run mum uniform of bootcuts, Next jumpers, Converse and warm coat. Then last year I discovered S&B and it was a huge wake up call. Within a month I'd bought Ash Jalouse, Hudson boots, grey skinnies, Becksondergaard scarf etc. I really couldn't believe how for someone who was know to dress nicely had let fashion completely pass me by for 5 years. In my defence my dc circumstances are a bit unusual and I'll use that as my excuse 
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My problem now is that I've started to discount stores eg M&S but was impressed by Shops finds. I need to be more open minded when looking for an item. Think it's because i have a crappy one near me.
Now I think I've got my fashion mojo back. Taking lots of tips from you guys, going for quality over quantity and being a bit more considered in my purchases as I've impulsed bought too many horrors.