I'm going into my third winter with the best boots I've ever bought: Ecco Voyage.
I first wrote about them here.
When I say going into my third winter, I mean I wear them every day from end of September til about April.
They may be slightly superfluous if you live in a city (you'd still find them useful though), but living in the country as I do they are fantastic and vital and here's why:
They look smart
They have a great grippy sole
I have a love/hate relationship with Ecco in that several of my walking boots that I bought from them (and my partner has had this same problem) have fallen apart after only a couple of years (not what I'd expect). But these seem different. Not cheap at £160 this year but on a price per wear basis they're a bargain.
And these are the socks to wear with them from Uniqlo. Warm, comfy, keep their colour in the way that other black doesn't (because they're synthetic but don't be scared of this, synthetics are so much better now). And they're not overly thick.
Not easy to see detail but they're these. £9.90 for two.