My top sport pairs:
The New SJ II is just an amazing pair that fits well and never seems to move on my face. They have passed the "wear on a roller coaster" test time and time again. Not only does it perform well, it looks wonderful and can be worn in a more casual setting. I would suppose that it is one of the most under-appreciated styles of the past few years.
Next is the Jawbone:
More hard core than the NSJ2, it fits the bill when I don't care if people give me weird looks while wearing it. If I'm uncertain about conditions, I always grab the JB.
SI Ballistic M-Frame 2.0:
The absolute most worry-free pair that I own. I can throw these around, and never be bothered about them getting damaged. They're made to be absolutely bomb-proof. There are no other Oakley sunglasses specifically built to stop shotgun blasts and flying shrapnel. The all technically can, but these were both purpose-built and tested to do so. It's nice that there is an optional strap, should you need it. Radars are technically a better pair, due to fit, hydrophobic coating, and such, but in my mind, the basic version gets the job done with its wonderfully simplistic nature. The lens clip holds the Ballistic lens in the frame more strongly than the original M-Frame or Radar nosepiece ever could. Furthermore, should I scratch a lens, they cost only $20 to replace.
Finally, the absolute king of purpose-built, sport-specific Oakleys, the Water Jacket:
All the functionality of a Racing Jacket, with the added bonus of hydrophobic lenses, venting, an all-around performance-based lens, and a strap so they never get lost. I've worn these snowboarding, biking, jeeping, etc. I actually haven't worn them on the water yet. It's a shame, really. They just don't get any better than this.