Autumn boots are one of those purchases that I've always felt it worth a proper investment. When its pouring with rain and you need to head outside, a warm and dry boot is pretty priceless. I used to really rate Clarks for my winter boots, and had a couple of great pairs that lasted really well. Sadly a couple of years ago I had to return a pair after a week of wear. Despite the boot legally being leather, it was actually that odd stuff where a very thin layer of layer has been applied over the top, meaning the leather 'skin' came away leaving a white underlayer showing. Horrible, and they're not cheap boots. I had quite an argument about returning them, but I did win of course. Not at all good enough for a £100 boot.
Anyhow, here is some winter boot inspiration, from companies I generally rate as investment purchases. Dr Martens was the most obvious first choice (see slideshow above).
I haven't tried Timberland but I'm betting they're a good investment boot too. Oddly I've struggled to think of other companies to explore, so maybe chuck some suggestions over to me!