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