Evening pipe is usually accompanied by some sort of fortified. Usually Port. I keep my pipe smoking as simple as possible, pairing tobacco and booze never crossed my mind. My smoking seems to be best paired to whatever I'm drinking. The opposite is also true.
I'd never drink something I didn't like. I'd never smoke something I didn't like. That's pretty much how I choose what to drink and smoke ... Something I like.
Pairing wines also seemed to be a waste. I like red and couldn't care less about the experts. I do red with fish, mutton, burgers, meat pies, shell fish, anything. I lead a rather uncomplicated life I guess.
I do try not to overpower my meal and save the Chateauneufs and Cabs for heavy red meats. Other than that, sky's the limit.