When we see Don backstage at the Stones concert in “Tea Leaves,” it’s a crystallizing moment because it shows like nothing else does how, to paraphrase Dylan,”the waters around (him) have grown.” Even Don, that hat-bound holdover, knows in 1966 wearing a hat is hopelessly uncool, but it’s not enough to save him. He’s off his game, walking on shaky ground, and whether or not he realizes just how much the tide has turned is something that can only become more apparent as Season 5 progresses.
Matthew Weiner has said that he always imagines Don will be wearing a hat, come what may, but for now, the nostalgia (and Don would be too old to appreciate its irony) of the Rat Pack redux is several decades away, and what JFK started by going hatless in 1961 has in 1966 come full flower. Sinatra and his ilk are “squares,” who are on the wane, and young men, who are starting to wear jeans to job interviews, wouldn’t be caught dead wearing a hat. Well a Beatle or Dylanesque cap, maybe, but that’s about costuming, which is inherently ironic and individualistic,certainly not as a di reguer accoutrement for work. The hat, like everything else, is rapidly becoming a symbol of the old order. Continue reading »











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