I would say it's about time you upgraded to clipless. Unless you like the cages of course.

For pedal/shoe system it will depend on a few things. Do you like to walk around sometimes when you ride? What level are you going to ride at(competitive, recreational. I say this because it isn't as important for a rec. rider to have the best shoes possible)?

If you want pure road equipment then the two most popular brands of road shoe I have seen around here is Sidi and Carnac paired with a pair of LOOK-type pedals.

Also depends on how much you want to spend, if you can give us a price range it would be alot easier.