Yesterday's junk is today's cool.
"Uncool" become the "New Cool" because the Nerd/Geek/Fool/Punk studies the culture, juggles the culture into their unique lives, tosses it into their behavior and re-arranges what is hip into the artful Modern New Cool. Hegel sees this as his triad of thesis, antithesis, and synthesis. We have a truth (what a culture considers cool) balanced by the opposite of that truth (what the rebels and reformers consider cool and the majority would consider uncool), synthesized into the new meaning of NEW COOL. A good example of this would be Japanese Fashion. Time progresses out of a synthesis between two extremes continually synthesizing into something fresher/newer. Yesterday's junk is today's cool.