In General
Think about kit by starting at your feet and working your way up and try to purchase items good for a range of weathers, so, layering is a good bet unless you want a wardrobe full of specialist gear you only wear a few times a year.
The more you spend the better the kit is. There are a few cheats that save money but if you want long life and reliable then do spend as much as you can afford. This will save you money in the long run. Buy from companies, where possible, that give a lifetime guarantee and be prepared to use that guarantee. My thermarest sleeping mat was replaced with no argument by Cascade Designs after two years of use…
Remember, if you won’t be winter mountaineering in Scotland then you don’t need a £450 waterproof jacket! Your usual use of the kit is what matters. If it’s weekend walking in the Brecon Beacons then a mid range waterproof will be fine.
Think about weight. Lighter is good but will be less durable. Are you solo backpacking? If so lightweight is very important. If not it’s not such an issue.
No boots are waterproof. Some resist water ingress a little better than others but the will all leak over time. Go buy some ‘Sealskinz’ waterproof socks. They are amazing.
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