He drove a truck for 20 years, but now he's got his own double-wide and a business vacuuming septic tanks, so he's doing ok considering he never finished ice cool.
1. to be the coolest of cool; this is the next level after 'cool as a cucumber'. People who are double cool with ice typically don't give a damn what anyone else thinks, can have fun anywhere/anytime, and give off such an insanely cool vibe that everyone else wants to be like them.
2. a way in which to order a drink if you want it in a very cold state.
Cools on Ice is used to describe something as cool but really it is the opposite/ is nerdy. This definition comes from the phrase itself, the phrase is obviously uncool but strangely cool at the same time.
When the phrase is said it is usually the case for the person he or she is with, to say Coolio. This is to show agreement with what the person is saying.
1) Those maroon and mustard bow-ties look cools on ice.
2) Person 1: "I can do a roly-poly in my room with out hitting my head on the wall!"