>>124217Might go for a straight stem if you're heavily bearded or mustached. You'll be learning to keep it lit and trying to pack it right, and you won't have the muscle memory for lighting a pipe.
Believe me, no tobacco tastes good with the smell of burnt hair. I started with a 3" mini pipe, learned my lesson quick.
Don't buy anything expensive or with a gigantic bowl. Try to smoke a giant gandalf pipe bowl full of tobacco and you'll make yourself sick. I'd avoid yello-bowl pipes (a brand of pipe that's pre-broke-in, if they still make them) because they affect the taste of the tobacco. A $10 drugstore pipe will probably do well enough for a first pipe - some people suggest corncob, but personally I never cared for them. Make sure to pick up filters if it needs them, and make sure that the filters match the pipe you're buying.
Pick up pipe cleaners. The first time you suck a mouthful of tar, you'll wonder why you ever thought this was a good idea. After a while, you'll learn when to clean the pipe, since every pipe is different.
Get a pair of needle-nose pliers if you buy a filter pipe. That filter is twelve kinds of nasty when you pull it out.
As far as tobacco goes, it really depends on what's available in your area. A good tobacco shop will have recommendations, but if you're stuck buying commercial stuff, I'd recommend Captain Black. It's not as good as what you'd get from a tobacconist, but it's decent.