I always have a pair of Timberland originals on the go for dog walking but I do wear down the soles on the heel every 3-4 years. They really are great at keeping you dry though. I recently bought some fancier antique leather ones from SC but the thickness of the elephant's arse leather on the bellows tongue makes them hugely uncomfortable and I've failed dismally in breaking them in.

I've got some Oliver Sweeneys for "car to coffee shop" jaunts and some lovely new Barker Lambourn in cherry grain for work (I don't wear a suit).

I was toying with some Grenson Ryans - anyone got any experience?