Walking the dog - what to wear - and where to walk?

I am new to dog ownership and I am fast realising my wardrobe is completely unsuitable for all-terrain all-weather dog walking!
I need some suggestions as to where to go to find stylish dog walking clothing that is practical and gorgeous in equal measure! I have my dog with me all day - so I need something that is smart casual enough to be good for work and walking!
Also - footwear! I really don't want to have to wear Wellies. Are there any less clunky alternatives?
And any good books, websites on best places to walk?
I travel quite a bit in my work and my lovely Jack Russell will be coming with me - so
would love to have some places to look for good places to walk, dog friendly pubs etc.
Hannah Quinn, London