There's a saying in Danish: there's no such thing as the wrong weather, just the wrong clothes.
Socks: I've been lucky enough to find excellent wool-rich socks by Ulvang in that TK Maxx place for about £2.50 a pair. If I'm going on a several day walk with all my gear in a rucsack, I swear by these Coolmax socks: they're great against blisters and wick moisture away very effectively. They're hard to get really clean as you have to wash them carefully...
Waterproofs: Instead of BC and AD we should have Before Goretex and After Goretex

I've got army surplus camo ones, which makes me look like a 'weekend warrior' but they're cheap and very tough (which is important as I sometimes crawl through hedges), although a bit noisy. I'd like to try Ventile but being a skinflint, I'll have to wait until I find something in a charity shop...
Recently I've picked up a really nice Craghoppers jacket which is fine in all but extended rain. I like Craghoppers Kiwi trousers too.
Underneath: if it's cold, a Pendleton woolen shirt or a decent fleece. I've got a Gore Windstopper one which is great, but it's a bit 'stiff'. It's really good on its own on a cold windy day and keeps the occasional shower out.
Hats: Sunderlands do a very lightweight one with in a waterproof-breathable fabric which keeps the rain out (and off my specs) but isn't much good when you sweat. In summer I use a reversible cotton cheapo against the sun.
Boots: my precious Lundhags ones finally gave up the ghost last year after 10 years and the third pair of soles. They're the best boots I've ever had but they're not cheap!
When I've got the cash I'll get another pair but until then I've got some lightweight KSBs, a stiff pair from 50 Peaks for when I've got my big rucsack on, and a very comfy pair of Karrimor Aspen ones which have enough space for thick socks. I also have a pair of Keen sandals which are great, but I find that stones, blades of grass and seeds get in easily. Your feet also end up filthy at the end of the day: the soles don't breathe so you get a nice mix of dust and sweat between your toes

Comfy though!
I get almost all my stuff on the cheap by keeping a close eye on the charity shops in town. One of the managers knows me and often puts the good stuff to one side for me

Paying less = less work = more time outdoors!