Lived in scotland for four years, lots of rain - Any pair of decent rubber soled leather boots + nikkawax = waterproof boots. It darkens the leather a bit, but that is it. Spray on waterproof works to a certain extent but not if there are big puddles, if you spray canvas trainers like converse they still won't be very waterproof. I have tried waxing canvas shoes, it worked ok but not as waterproof as a leather boot. A small umbrella is fine if there is no wind, in stronger wind you will need something more than a compact umbrella and if it is very windy umbrellas don't really cut it in which case you need a raincoat with a hood or a hat. In very heavy rain or if you are going to be out for a long time a waist length jacket won't cut it - you end up with soaking legs. I have a barbour for lighter rain, I think they look pretty awesome and so long as you wax them every few years they are pretty much waterproof. If you don't like waxed cotton they do offer unwaxed waterproof versions of a lot of their jackets and also summer weight ones. For really rainy days or if I am wearing a suit I have a mid thigh length trench coat, which is longer than seems to be fashionable, but more practical, and a flatcap.