Had a 944 convertible. Loved the way it looked---Wasn't a fan of the hatchback's look either. Lived in CA. Always wanted a top down car.
Despite wanting a convertible so much I found driving top-down was "meh". On the one hand I could enjoy the view on Route 1. On the other, it got hot and I found the wind annoying if I had a passenger. The idea of a convertible proved much better than the reality.
Went to check the Boxster as soon as it came out. Frankly, I was disappointed in the way it looked. With the top up the rear half of the car just didn't call to me. Neither that or the fact it was a convertible is not why I didn't get it. Embarrassed to say I found the clutch to be too light with an oddly high point of engagement. Ended up with a 996.
Then, the Cayman came out. Those hips and the sloping roof fixed more than just the Boxster proportions that I wasn't wild about---I thought it was the best looking car Porsche has ever made. But a move to Montana necessitated I find 4 wheel drive sports cars.
Each generation of the Cayman was as good looking as the last. And after a VW R32, Audi S4 and Golf R (modded all the way up to a big turbo), and a beater Honda Element to handle the winter it was time.
Done. And couldn't be happier.
I will say, though, that the Spyder's shape is a close 2nd to my eye. Whatever you call those protrusions behind the seats, WOW.