OK... I have a few, each with a different purpose.
First expensive pair of sunglasses I had were some cheap Oakley metal frames... forgot the exact model, etc. Don't wear them anymore.
I also had a pair of Magnesium M Frames, which are no longer in production. They were stolen (while in a church!). If you like the M Frame style, and don't mind paying extra for nice sunglasses, AND you can find a pair, these are the premo-oakleys in my opinion. They discontinued them because they were expensive and probably didn't sell many--why go magnesium when you can go $150 cheaper with the mframe?
For baseball:
Oakley Pro M frame.
Pros: Best for the job. I see fly balls better with them and won't play outfield without them. They can stand a little abuse... not that I put them through much. These are the pro glasses that MLB players use. Interchangable lenses for varying light conditions
Cons: Don't bend (i.e. difficult storage/carrying, but the regular M Frames do). Very job-specific (baseball, shooting sports, maybe golf). $$$.
Notes: Buy polarized and don't look back.
OK, you'll think this is really strange... but when I have a really short haircut:
Persol somethings... Daniel Craig wore them in Casino Royale
Pros: Bond wore them. High quality optics
Cons: Prone to scratches, $$$ for a pair of glasses I rarely wear. Hard to find.
And my kinda wear-everywhere, don't-care-if-I-scratch-'em Ray Ban's.
Pros: Reasonably priced (<USD 120; can be found for ~90). Classic. Reasonably tough, easily replaced. I feel comfortable wearing them anywhere because I've relegated them to eventual destruction.
Cons: Everyone has a pair of aviators. (hyperbole, twitchy forum members)