Well, I guess for me, it started off with what my guitar heroes played. I saw Dave Murray (Iron Maiden) playing a Fender Strat when I was about 12 years old, so just assumed since he played one, they were good guitars. The same went for Dave Mustaine when I saw him in a video playing a B.C. Rich. I just assumed they were good guitars since he was playing one.
So, naturally, for me, I wanted to be like my guitar heroes, and latched on to Fender and Rich at a young age. I thought those guys were cool, I thought their guitars looked cool, and I wanted to be cool like them.

ccasion14:
Time went on, and naturally, I wanted either a Fender or a Rich. I got a Rich, and I like the way it plays while I'm sitting, but when standing, it's another story. It's quite top-heavy. I also wound up with a Fender Tele, but I'm really not quite sure why. I've never been a particularly huge fan of them, and quite honestly, I'm really still not. :icon_scratch: I much prefer the Strat to the Tele, but mainly just because of the looks, more-so than for any other reason.
As for Gibson, a buddy of mine had a LP, and I just absolutely hated it from the moment I picked it up, even before I played it. It was super-heavy, and always felt "slippery" while sitting with it. There was also something about the feel of the neck that I never quite connected with, yet I couldn't tell you what it is. The LP's neck just doesn't feel "right" to me. That's seemed to carry across their line, because I've never played a Gibson I've connected with. I have an Epiphone acoustic, which my wife purchased for me, and while it holds sentimental value for that very reason, I really just don't like the way it plays at all. Gorgeous guitar, but just...blah.