I've been into Oakley since I was 9. Here's a rundown of the sunglasses that have passed through, or stopped at, my hands.
Frogskins (1st gen)
My first pair of Oakley's were Frogskins. I wasn't really into this stuff but I was (and still am) into frogs and somehow I was introduced to these via the Frogskins catalogue at the time. I can't say I necessarily liked them for how they looked but liked the name so wanted it.
I can't quite remembered exactly how much I saved up as a kid, in the $140 neighbourhood sounds right, but there was the one-and-only sports store in the small, shithole town I was in back East that carried the brand. I couldn't decide on what colour frame to get, not that there was a lot of choice back then, so I went with no colour and got clear. The lenses in em at the time were the fire iridium's, but I left 'em in my jacket pocket snowboarding one day and both lenses got scratched to shit. It's probably why I'm a little more paranoid about my shades now because of that.
I special ordered a different colour of lens from the same store (I think for $40 - $60?) and at the time had one-of-a-kind custom Frogskins before there was were options to customize Oakleys. I liked blue even then and got the ice iridium colour.
I think subconsciously I never wholeheartedly liked the style, just the name, and I believe I sold em to one of my brother's friends so I could buy my next pair off my him.