How do you create a wardrobe that combines a love of the outdoors but is still suitable for working in an office and living in a city?

I am a pragmatic function over fashion kind of guy who wants a day to day wardrobe that meets the demands of living in Scotland where it's both wet and cold more often than warm or dry.

In particular I need recommendations for trainers/shoes that are relatively waterproof as my sketchers get wet when walking the dog.

Otherwise I'd like to hear other recommendations that fit the general point of this thread.