The easy-wearing, careless style of the loafer is an American classic (even if schooled abroad) and a direct descendant of the shoes humans slipped on when they first sniffed at going barefoot or wearing sandals. Real cave men wore moccasins, and since the 1930s when they began being fitted with hard soles, low heels and various decorations on the vamp, so have generations of American men.
The modern loafer-style moccasin came from a Norwegian iteration apparently worn by dairymen. The Spaulding Company, which trademarked the term loafer, first made them in America in 1933. A few years later, Bass Shoes started making similar models, but called them Weejuns, a contraction of "Norwegians." The origin of the loafer tag is more vague. The derivation may be agricultural (the dairy farmers wore them in loafing sheds) or be a corruption of a German word meaning wanderer or simply derive from the general attitude that comes with wearing a shoe that one needn't lace.
It was Bass that added a saddle strap with the slot into which a coin could fit (hence penny loafers). It wasn't long before others copied and further adorned the front of the shoes. The look, which was debonair when Hollywood royalty—e.g., Cary Grant, Gregory Peck and Jimmy Stewart—embraced it, turned very cool on the feet of bad boy James Dean.
But, let's face it, despite their provenance the shoes now have something of a wonky image. Penny loafers were also the shoes of bobby-soxer girls, who kept dimes in the coin slots for emergency calls before people carried phones and booths charged a quarter. Standard models carry the preppy stigma and the Gucci loafer, with its horse-bit hardware, is maybe a little bit too equestrian wannabe. Another variation, the car shoe, is the stuff of soccer moms. And the tassel loafer, well, it was forever damned when George H. W. Bush, himself of pure preppy pedigree, accused opponent Bill Clinton of being the candidate of every "trial lawyer who ever wore a tasseled loafer."
So how to transcend the stigma and enjoy these shoes for their innate comfort and style? Crocodile. In this handsome yet durable exotic hide, the loafer shows that your footwear has grown up and you are a force to be reckoned with. Zelli by T. Mantzel provided the example shown here (Renaissance in brown, $750) and makes several other crocodile dress slip-ons as well as casual models in varying skins. All are made in Italy.