There is wisdom in this, true, but it's not common wisdom. And there aren't enough of the wise in this world to make up for the perfect crapstorm you get from the unwashed hordes. If some of the unwashed hordes are in control of some aspect of your life (like employment prospects), you have to decide if the admiration of the "cool few" is worth it. Simple cost-benefit analysis, really. "I gain this, I lose this. Is the final sum positive?"
I am wondering if this will change in the future. When everything can be found out about everyone, would the net result of so much knowledge not be that it devaluates? Will there come a time when people accept a certain number of drunken facebook pictures because they can be found for everyone?
And if we stay with the costs analysis: The costs of keeping a clean slate are very high. You have to be in tight control of your life every step of the way. You don't have to read Freud to imagine what might happen at some point.
I do not deny that we are social creatures that judge other people. But what we use to base our judgment on changes over time (not necessarily for the better, it just changes). Women can show their ankles these days, but there used to be a time when that was shocking and/or arousing.