I've had a few Oakleys for a couple of decades now, but I never really considered it a collection - I have collections of other things, but the sunglasses just seemed like something I had a few of.
Started off, as perhaps many did, on Frogskins in the early to mid-90s. Still had my favourite pair around until recently, crystal black with +red iridium, sitting conveniently in the knee glovebox in the car. So conveniently, in fact, that I'd sometimes forget they were there. Like when trading the car in for a new example for instance :( Someone somewhere is driving around with near mint Frogs in the car and they probably don't realise either...
After the Frogs, I was quite taken with the... New Frogskins. Ok, the name sounds the same but they don't really have much in common and it's not a model you hear much about. Two of mine have suffered from cracked frames for years. Maybe it's the sign that it IS a collection that I could never make myself throw them out, even though they weren't wearable...
So, with two cracked pairs, and the matte clear showing signs of going the same way, I decided to check out what was happening in the Oakley world about 15(!) years after buying my last pair. I thought I'd go Frog again, but they didn't seem quite right any more. Besides, it would be a little unfaithful to the pair travelling around in my old car! But I wanted something in the same vein, and Holbrooks hit the mark pretty exactly.
I like "vertical" collecting (single manufacturer, single model) so had decided to focus on the Holbrook, but then my first pair of Juliets to scratch a long-standing itch came in. And were just so perfect in terms of look and fit, that that is where I have stuck for now. Just about to hit another milestone in terms of Juliet collecting, but that's for another day...