For some guys, only a pipe big enough to cover their entire face can help.
If you only smoke setting in your garage or livingroom, what would it matter.
But, what I have noticed smoking at the Briary, is that seeing a big huge guy with a tiny little pipe is as ridiculous as seeing a small little guy with a huge honker of a pipe. And, it is even funnier if the two are setting side by side.
Me, if I am smoking on the tractor or alone in my studio, I don't care. But, I will grab pipes that my wife thinks look good on me if we are headed out together. I have no idea what qualities make a pipe "fit me" but I rely on her suggestions, as I am not the one who has to look at me.
All that said, I do prefer the image I project with a straight pipe to a semi-bent over a droop down my face flaccid bent pipe. Like ties, the things we adorn ourselves with give off subconscious Freudian cues.