In my experience I have always let my styles and techniques evolve as needed, and since I have always come out sounding only like myself, with my own style, I have always trusted my ears, hands and the progression that they take. This, in recent years has also been true of my assimilation of Jazz. The problem with only “concentrating” on one particular musical vein is that you end up sounding exactly like that! These days we are filled up with those people who dove head first into Jazz, leaving all other style behind, and they really pretty much all end up sounding the same. The real problem, (and this applies to blues as well) is that what we are hearing and learning now is all at least 3rd or 4th generation down the line, and instead of the music being fresh and new, it’s all been worked over and analyzed to death!
The very nature of Jazz means experimentation, and it’s not the goal to just “sound like” a Jazz player, but more to simply be one! I can recall years ago when I was playing at Lincoln Center with the African singer, Tony Bird, a man came up to me and said “you know, you play in the truest form of Jazz tradition!” This really kind of turned me around, because at that time “Jazz” seemed like a mystery to me, and I felt just about as far away from it as possible. But what he made me realize and see was that I was a true improviser, and that I never did the same thing twice. My quest was already to be as fresh and as creative as possible, and even though I may not have been using a ton of flat 5s or sharp 9s, I was already maximizing everything I could possibly use with my knowledge base.
As time has gone on, I have left myself more “open” to the sounds of Jazz, and can now much more easily recognize what a player who used to baffle me completely, is actually doing! This is a wonderful revelation to feel, but it’s really not that much different from listening to a Country player or Blues player and trying to emulate them. It’s just a question of, amongst that “blur” of notes, to be able to recognize something that you can “hang your hat on” so that you can get a sense of what is familiar about the “unfamiliar!”
It also has to come from you no longer being afraid to play some wrong notes, because that is bound to happen. You will, and must learn from your mistakes, and there’s tons of “trial and error” in assimilating Jazz or any style for that matter. Make sure to start “hearing” your intervals, and learn to recognize tonalities such as 6ths and 9ths, major 7ths, sharp 9ths and sharp 5ths, to name just a few. Listen to single-line players, such as Coltrane, Louis Armstrong and Miles Davis. These people couldn’t play chords like guitarists, and they had to rely on “shaping” their phrases. This will help you do the same. Eventually, you’ll be able to listen to a complex Jazz chord, and say exactly what it is, understanding all of its tonal relationships! So I hope you really “go for it”, and can acclimate yourself to blending Jazz into your style. Many great guitarists have…just listen to Hank Garland or Danny Gatton, T-Bone Walker and many others, and you’ll see what I mean! Good luck!