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I went through a stage when I bought lots of clothes on impulse (call it retail therapy - I was having a very difficult time) that were not even that nice.
That period has passed but I still make mistakes. My biggest one is shoes - so many times I have bought shoes that turn out to be really uncomfortable. I was just thinking about this today because I bought some new boots recently, after a lot of consideration, that I thought would keep my feet warm and comfortable. Wore them today for the first time and the lining is itchy, and they feel very stiff!
My Hobbs jacket. Because I'd hit that age (50-ish) when people start telling you it's better to spend more on fewer, quality pieces. Worn twice.
My Jigsaw tailored wool, A line coat. Because although it wasn't the one I liked the best, it was a classic and I'd wear it forever, yak, yak, yak. I didn't and, in any case, the cuffs frayed after two years.
That said, I think making mistakes is part of style. If you're too afraid of making them, you never try anything new.
A Superdry chunky knit cardigan. Cost £75. It was most definitely a silly splurge for me - I'd never normally spend that amount of money on a bloody cardigan. It's so chunky and heavy it's stretched out of shape, isn't even warm, it's really itchy, it's gone unbelievably bobbly and looks old and tired even though I've barely worn it.
I won't chuck it out though, purely because of how much it bloody cost! I make a point of wearing it every now and then but it's not long before it's thrown off!
Recently bought a new Olaz / Olay serum ( anti age snake oil shite) for double digits, after a long time comparing and deliberating —watching YouTube—
Wore it in combination with my normal makeup (moisturiser, foundation etc), got to event and had tide marks and peeling / rolling makeup on my cheeks and forehead. Feel like an idiot now. I looked rubbish
I had the most beautiful hobbs coat many years ago. It was the most beautiful shade of deep red. It was a present to myself after finishing my degree and got a job. It cost more than anything i have ever bought and it was beautiful boucle material - frock style with a deep red silky lining. Even better it was a size 10 even although i was a 12!!!! I wore it very little as it really didnt work with my lifestyle and then flogged it on ebay a good few years later at least but for a song <weeps>
I bought a coat last year for loadsamoney, thinking it would be useful. And, it will be, for the next 30 years, it will be, for funerals. I am ageing and it will be brilliant and have lots of outings, but I do wonder whether it was the right decision. Of course, it will do lots more too, but it hasn't been worn yet.
Also a pair of boots, very very expensive ones of the leather/suede welly type - French for "camel". They were stiff and uncomfortable, even after several wears, and the zip seemed cheap and nasty and made a clinking sound when I walked. Sold them on eBay for a fraction of what they cost me.
And yes, more creams/potions/make-up than I care to mention that has brought me out in eczema and rashes.
Cherry Dr Martens Chelsea boots (not Floras but the unisex very round toe). They were 80 v 120 for the Floras which are slim and neater fitting but I bought these for price. They look a bit like clown shoes.