Agree with William. For context, I've never heard anyone us "rolling in the deep" ever, until the Adele song. Even then, I've never heard anyone say it in actual conversation. Rolling Deep is pretty much slang though - most people wouldn't understand it. But William is right - large group of people going out together.

"Roll deep" means you are going out with a large group of people. So, 'my clique rolls deep' means that a group of exclusive/popular friends are going out together. "Rolling in the deep" means something else though, has to do with being very deep in love, or feeling something very strongly.