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!"