The truth is, penny loafers never really go away, they just vacation on the coast of Maine when the sartorial going gets tough. From time to time, however, penny loafers reign supreme – in the 1930s when they were invented, in the 1950s as worn by Montgomery Clift, in the 1960s, when sockless American campuses made them de rigeur, in the early 1980s, when the world went preppy. Penny loafers are stayers, as likely to disappear as, um, a bad penny.
Penny loafers are a quintessentially American shoe, as American as wooden clogs are Dutch. Too often associated strictly with the Wall Street banker’s grey flannel suit and rep tie, penny loafers are perfectly acceptable and a much better option with jeans (straight-leg Levi’s or a few narrower fits), shorts (either roomy Bermudas or thigh-revealing tennis shorts) and khakis (we like J.Press, but you’re just about safe with the Gap, if you’re young).
The question, of course, is which penny loafer to go for. When recently faced with this dilemma, I stuck with what I knew and opted for Weejuns. As a youth, I only ever wore Weejuns in burgundy, as traditional as it gets. This time, a little older and wiser and feeling a little whacky, I opted for black Weejuns with a beef roll. That little extra chunky bit of leather always makes me smile. I can’t tell you how pleased I am, and I reckon most people that see me in them are, too. At about $90 a pair, you can afford to wear them everyday, even though you probably shouldn’t.
Weejuns aren’t the last word in loafers, alas. Michael Bastian – a designer who understands men and whom we much admire – recommends Alden. They’re smart and well-made – go for their Leisure Handsewn Moccasin in burgundy calfskin, though the Penny Loafer Flex Welt in dark brown suede is good, too. If you’d rather not fly to America for your shoes, and want to get something British and reliable, look seriously at Crockett & Jones, who do ever so many styles – the Boston in Tan Scotch Country Grain leather is snappy.
One rule: don’t put pennies in your penny loafers. That’s what teenage girls do.
If you have favourite loafer we ought to know about, please do tell.