Let's take the Duke of Windsor and Agnelli, just so nobody really disagrees that they were great. Now consider their overall style and their innovations. Three things jump out at me: They broadly blended in among people of their age and social group: suits when everyone wore suits, etc. Most if not all of their innovations and breaks from the rules were away from formality and towards a more casual look. They could get away with innovation even in their more dress code-bound world because people knew who they were. They had next to nothing to prove. On the other hand, your typical iGent (especially those who don't need to dress formally for work): Sticks out like a sore thumb in a crowd of his peers. His deviations from the norm tend towards more formality. Tries to be appreciated for his dress sense as a freestanding quality. (Ok maybe this isn't always true.) See, we're aping the greats' style but we're not following their example at all. We're doomed.