I never liked the military flat cap trend that ran for a few years I think around 2006-2009 or so. Lots of people rocked them but it wasn't my thing.
Best hat game, randomly who comes to mind is Kevin Coakley, I remember he was running snapback caps around 2011-2013 or so when they were first making a resurgence. I might be off with the dates, but it was when things were shifting from New Era caps back to more form-fitting snapbacks. I always loved Starter caps.