Really, great idea to start this thread...too easy to get negative about specific shapes you don't like, and why.
I honestly think, for me, it depends on the briar grain first, and shape later. Then there's holdability, clenchability, what I'm doing at the time, etc...
Lumbermen, Lovats, Canadian, Liverpools and their ilk are wonderful: if the grain and cut is right. The more wood shown off, when it is good, the better. The design is capable to show off great rustication and texture, too. Wonderfully sleek, lightweight to carry, good length to keep smoke out of the eyes...
I like apples, pears, pots, brandies, and billiards rusticated or finished roughly--though they can show off a nice grain, they're a great shape for the hand. Especially if they're on the heavy side, they're great smokers. Great pipes while sitting, and if made to sit (but not necessary).
Freehands (love that plateau), whales, fishbowls, eggs, volcanoes and other atypical, avant-garde shapes are there to look at and appreciate the feel of the angles. Everyone already knows I love weirdo pipes. Sometimes cumbersome or funky, they have an appeal to me that is more curious to go investigate than anything. Extra points if they happen to mesh well with my smoking habits and fit in the hand--I've found most of them somewhat inconvenient to travel with or clench. Sitters a plus.
The "cylinder" lines are ones that appeal to me a lot: Pokers foremost, sleek yet playing off those 90° angles and convenient to set down... dig 'em! I also love a good cutty and Dublin! :cheers:
My favorite "utilitarian" pipes: Best is the bulldog, hands down. One with a slight bend, especially. (cheers, Harlock!) Rhodesian and other formats as well. Few pipes look like as sporty as a nice bulldog, regardless of the grain or setup--I love 'em. They are artistic, yet simple, great for being on the town. Runners-up are Diplomat-cut MM cob, and spiffy panels!