Maybe. Maybe not. You may come around to Chet someday. Then again, you may *never* really enjoy his work. I used to say that the difference between Miles, Chet, and Tom (Harrell) (all of whom have a similar middle range trumpet style) was to say that Miles sounded stand-offish, Tom sounds abstracted, and Chet simpered. To a certain extent, I still think that's true. There is something almost "effeminate" about Chet's playing (not that there's anything wrong with that B) ), just as his voice is somewhat androgynous (people always ask me if that's a man or a woman singing when they hear Chet sing for the first time). That can be a bit off-putting, I'll admit, but I don't think that it stems from any preconceived notion of "manliness". Chet played the way Chet played. Either you like it, or you don't. I didn't like it, now I do. Why? I don't know.
I highly recommend Chet's Prestige albums with George Coleman. You can only get them as imports, but they're not too terribly expensive and they are usually available through Amazon.