This is quite the discussion - I came in late, yesterday, read some - don't have time to read it all. Thought I might throw in my $.02 worth, anyway.
When I started smoking a pipe, as a college student, part of the reason was that it filled my image of being a "college man". (I never smoked cigs, and nobody in my immediate family smoked at all.) I bought inexpensive, fairly traditionally shaped, drugstore pipes, with no conscious thought about anything other then price.
These days, as a retired widower, my 99% of my pipe smoking is done alone. I still gravitate to traditional shapes. I don't smoke a lot of really large pipes - have very few above about a Dunhill group 4. If I ever bought a pipe for a reason other then "I like it and it fits what I am looking for", I am darned if I know what it is!
Seriously never thought of it that way. Though I have thought this pipe looks stupid in my face before. Thankfully like most pipe smokers I have a tangible aura of fancy pants which counter acts the silly look of stuffing ones face with a burning chunk of wood.
To save you the effort of reading through- there was no final consensus on whether there's any merit to choosing a pipe to suit your face. Although, a few members of this forum gave it more sway in their selection process than I personally expected.