You've got to hand it to ol' Daniel Boone: The man had class. He hated coonskin caps, which were sort of a precursor to the Trapper's Hat (below). Boone wore a battered felt hat, instead, but the coonskin cap still caught on. Davy Crocket wore one, as did Fess Parker when he played Davy Crockett on TV. Meriwether Lewis may have worn one on his journey of discovery. A portrait of him painted a year after his return from the West shows him in a fur cap with not one, but two, tails. But consider this: Scut Farkus, the bully Ralphie beat up in A Christmas Story, wore a coonskin cap. So did Uncle Fester in the original Addams Family television series. So, think about that when you see one and think, hmm, maybe? Maybe not.