Well, I started on an inexpensive Alvarez acoustic. I thought that was all I would need. Then I got the itch to try out an electric. I still was in my infancy with guitars (it was 200o) , so I picked up a First Act with a bridge humbucker, and a little First Act practice amp. That started the electric bug and I went with a Dean Evo XM with dual humbuckers next - loved the feel of the neck.
I played that for about a year, and then bought an Epiphone LP, and shortly after picked up an Epiphone SG, and an Ibanez AS73T
Along the way, I picked up an Oscar Schmidt OE-40 as my first hollowbody. It was nice, but I never quite had the place to play it.
I had tried a few Strats, but I just didn't like the feel of the necks, so next came a Schecter C-1 Elite. I was still all about the feel of the neck, although notice I was still all about humbuckers.
Next came the Strats - SSS and SSH (only the blue one remains, of these 3)
Bought and American Tele, but I never really bonded with it
Then I went back to acoustic, and picked up a Takamine 12-string, just for kicks. It turned out that this is a guitar that I continue to use, especially when I am playing with another acoustic.
Played an Ibanez AM93 a few years ago, and it has replaced the AS73T, although it's mostly just played around the house. I also picked up a Peavey Limited HB USA, and it has really replaced the Epi LP for my solid body dual humbucker sound.
In the last couple of years, I traded in quite a few of the guitars on a Taylor 710ce, picked up a Fender Deluxe Player's Strat, a Takamine Glenn Frey Signature A-E, a Fender Special Edition 60's Strat, a PRS just for giggles, a Squier VM Jaguar.
I haven't been playing for 30 years, so I still explore sounds, like I did when I began playing, but I am beginning to narrow down my tastes. I don't have as many as I used to have, because I recently thinned the herd quite a bit.
Oh, and I can't believe I forgot the Gretsch 5420 that replaced the 5120. I love playing this one with Beatles tunes.