Used to find the idea of spending upwards of £50 a lot already. They’d start falling apart after a few months and would either not be waterproof as they claim, or the winter ones I bought would still be cold and uncomfortable.
Last year I bought a decent Jack Wolfskin waterproof winter coat for £130 and took it to Munich in January. It snowed (a lot) when I was there and during/just after the heaviest snowfall, I spent the entire day wandering around Munich Zoo in the freezing cold, never once did I actually feel it. It also looks great and feels like it’ll last me a long time. Probably one of my best purchases in years.
My other one would be shoes - walking shoes, running shoes, football boots, anything footwear wise. I’m flat-footed and overpronate quite heavily. Before I figured out why I was getting pain so badly in my shins that sometimes it would take me 10 minutes to stand up in a morning, I was buying any old trainers and shoes - quite a lot of them in fact, because I’d find them highly uncomfortable after a week or so of use and decide I needed a new pair.
I bought some Brooks trainers (from the Adrenaline range) after having my problem analysed in an Up & Running store and have been close to pain free since, it just costs me a lot more than I’d hoped, but overall less than randomly buying and hoping for the best.