This image (another find by comment-leaver Carmelo in the Esquire archives), came with a date but no caption. So I decided to give it one for the headline above.
It’s easy to think of penny loafers as a casual shoe since, in the grand footwear scheme of things, they are. But much of the charm of Ivy-preppy dressing is the mixing of casual and dressy items. The postwar legacy of the Weejun is that it is a shoe to be worn with khakis and a blazer, or sockless with a madras shirt. But in the Weejun’s infancy (it was introduced in 1936), when men still wore hats and gloves and overcoats, the shoe was able to hold its own among these more formal sartorial items.
So if you’re looking to put a new spin on the old staples in your wardrobe, try this. Next time you put on that winter topcoat and hat, don’t reach for the tassels or lace-ups. Penny loafers did the job just fine before the war, and they can do so now. — CC