This may look like a penny loafer graveyard, but the Dexter shoe is apparently alive and well (sort of). Though the company doesn’t have much of an online presence, there’s a 1957 collection, named for the year of its founding, available from Shoeline.com.

The above ad is from 1965. Below is one from 1966, which features some handsome tassel moccasins as well as those ghastly Venetian loafers, which are like a face with the eyes, nose and mouth missing:

But the Ivy heyday was coming to an end, and by 1967, foreshadowed by the previous graveyard imagery, the Ivy League Look was roasting on a funeral pyre:

So in 1968 the company went international. No more penny, tassel and beefroll moccasins; now there’s just a single bit loafer:

You can see where this is headed. Fast forward to 1971, when the ad design — as well as Dexter shoes — would look radically different. — CC

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