This is just such a subjective question.
I own a lot of pipes: British, Italian, Danish, German, American, Cobs.....you get the idea.
I want to say that J. M. Boswell, an American pipe maker in Chambersburg, Pa., makes one of the finest smoking pipes (IMHO) in the world.
Top quality briar, aged for years. Great hand-carved skill, innovative and imaginative designs.
Smokers complain that when they purchase a pipe, a cotton pipe cleaner won't go through stem, shank and to the bowl.
You will not ever have that problem with a Boswell pipe. They are drilled perfectly and they smoke great from the get-go.
In my experience, the pipes smoke like they should from the first bowl.
Break-in is not the dreaded tongue lashing experience of most other pipes.
Check out Boswell.com