Birth Of The Cool


This Esquire illustration was recently posted to Ivy’s Facebook group. It obviously has great visual appeal, but I found it especially interesting for the date: it was drawn in 1942.

Now you can see the ’40s-era drape in the cut of the blazer and the trousers. And of course by the time the Ivy trend took hold a dozen years later, double-breasteds had all but disappeared from the male torso. But the shirt is madras, and the overall vibe — the sunglasses have a lot to do with it — has a cool ’50s feel. The guy could be hanging out at the Newport Jazz Festival. He could be Dickie Greenleaf.

And in addition to the detail of the two-button cuff, the outfit has something else that’s in keeping with the Ivy and prep approach to dressing that rose in the following decades, and that’s the mixture of the formal and informal. For those of you who have a DB blazer stashed in your closet, remember that you can bring it out for more than just dressy occasions. — CC

14 Comments on "Birth Of The Cool"

  1. Robert Armitage | March 13, 2019 at 3:33 pm |

    1942? This guy should have been on Guadalcanal, not giving off lizard vibes at the Beverley Hills Hotel.

  2. Marc Chevalier | March 13, 2019 at 3:44 pm |

    @Robert Armitage – Bone spurs, perhaps.

  3. @Marc TDS – He really does live in your mind rent free 24 hours a day – amazing!

  4. Cool illustration. He reminds me a bit of young Robert Culp.

    Best Regards,

  5. Hardbopper | March 13, 2019 at 4:56 pm |

    @ S.E. Hilton 59 is my all-time favorite.

  6. Hardbopper | March 13, 2019 at 5:03 pm |

    @ S.E. Hilton 59 is my all-time favorite. The haircut, too. Ivy league #1, not quite two weeks old.

  7. Christian – you should do an article on the Farmer’s Life Insurance guy on TV. We know a thing or two about insurance because we’ve seen a thing or two…

  8. Carmelo Pugliatti | March 13, 2019 at 7:05 pm |

    The interesting thing is that this is a “Kent” (Button two, show two) double breasted.
    In “Ivy”trend age the Kent DB blazer were still sold.
    In 50s on “Gentry” magazine and “Esquire” you can see a lot of kent blazers and also four buttons (Button four, show four) double breasteds.
    Many of these were “ivyzed” (natural shoulders,undarted,narrow lapels,narrow wrap) So a not different outfit could be wear at newport in 1956 or 57.

  9. Any recommendations for a similar pair of sunglasses?

    The Gregory Peck model from Olive Peoples is the closest I’ve found:

  10. Carmelo Pugliatti | March 13, 2019 at 7:10 pm |

    Crimson | March 13, 2019 at 7:07 pm | “Any recommendations for a similar pair of sunglasses”?

  11. Old School Tie | March 14, 2019 at 8:12 am |

    You cannot see, but it is almost guaranteed he is donning my favourite type of trousers……..pleated.

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