Deciding to expand the shoes’ reach in America, they teamed up with G.H. Bass and retailer Rogers Peet to get it done. By 1936, the Weejun—a playfully shorted version of Norwegian—was born.

It didn’t take me long to figure out what kind of loafers they were: G.H. Bass Larson Weejuns, of course. I’m convinced that if you put a handful of people all wearing black penny loafers into ...