Good morning, Erin.
What you're wanting to do is gain popularity - to be cool - by imitating those whom you see as having it. However, in your deepest self you know that this won't work - you are searching for your own sense of style. You want to be a trend-setter (this is the significance of Kelly Osbourne in your dream), rather than a follower - and this is just fine. I've always believed that people should be very sure of what they want before making permanent (and painful) decisions.
Good luck with it, and let me know how it goes.