Before I quit smoking, I was very heavily into pipes and really fine tobacco. Pipes look neat as accessories to whatever you do (except maybe swimming and SCUBA), and give you something to do with your hands. I always thought anyone that spent time in the outdoors (especially hunting) needed a pipe to complete the package. Pipes look good with guns and knives.
While English briar, Eastern European briar, Danish briar, and Turkish meerschaum are supposedly the best, I had some very nice ones made from Irish briar, Israeli meerschaum, and Italian briar. My favorite was a large bowl briar crook-stem from Ireland.
Spend time with your tobacconist. Give him an idea of what type of pipe smoker you are, i.e., beginner or old salt. Also, believe it or not, if you let him know what type of pipe smoking experience you'd like, he can recommend a tobacco. In fact, he can blend just about anything you want, and it isn't really expensive if he is using the house blends. My personal blend was comprised of a house blend coffee/chocolate burl cut and a small amount of virginia cut Latakia. I think it was around $2.25 an ounce.
Another thing that most people don't know is that pipes can be restemmed and refurbished. Often a tobacconist will have a selection of used pipes purchsed from an estate, which he will restem and refurbish. Some pipes of considerable value can be obtained for fraction of their worth because they are "used".
As a last thought, if you buy a new pipe, remember that it will take a few bowls of smoking to get it broken in. Which is another reason why restemmed pipes are so good - no need to break them in. Oh, and stay away from meerschaum until you've had some experience. They tend to burn cold and often required a lot of relighting. And if you really like pipe smoking, try to get more than one pipe, since it helps to rest them a few days.
Wish I could still smoke, but even day-old bar smoke makes my lungs do bad things.....