I've got Asolo powermatic boots, very firm and heavy leather, I'm still wearing them in, but they are very supportive of the ankles.
I don't mind wet weather, now that I have all the proper gear. I stopped scrimping and decided to invest in my hobby - still cheaper than the gym or even a bike in initial outlay and upkeep, I reckon, as once you have the stuff it generally lasts for a few years.
I got fed up with big and bulky coats, now have a cyclists waterproof jacket keeps the wet out, breathable but only weighs a few grammes and squishes up to tiny bag when not in use. Combined with waterproof trousers over running tights and merino base layer top, I stay super warm and dry.
Tired now after my early morning walk, day at work and yoga this evening, but at least I will sleep well!