I can't afford to buy expensive boots. But I can recommend a nice pair of Brasher Goretex walking boots - I wear mine on most cold days (and they are one of the most comfortable shoes/boots I've ever worn) or days like today when almost anything goes in the office :)

For me, it is all about comfort, and I could not put up with any shoe that needs a disproportionate amount of time "breaking them in".

I do like the look of some of the shoes/boots on this thread but doubt I'd ever spend anywhere near the amount some cost - I think I'm just a cheapskate when it comes to shoes.