I remember wearing my first pair of Penny Loafers in high-school. Attending a preparatory school made it pretty typical to have a pair. It was effortless to fit right in, layering with an Izod sweater (this is of course when Izod owned the alligator) and designer jeans, designers like Calvin, Gloria and Jordache. Oh, those were the days. We were all the quintessential 80’s preppies and we all properly wore penny loafers. Here was a time that I’d also like to forget since fashion with all it’s unexpected “creatives” was non-creative.

The Penny Loafer has come a long way. There really is no other shoe that has traveled so many paths and has crossed over to the iconic status of classic. From 1960s on campuses where male students did not wear socks, even in winter, to the 1970s where it became a "class style" for men to go dancing in loafers, without socks. And then it was my turn, in the 1980s when the preppy look made the penny loafer young and genderless to nowadays where it is a classic to wear. From man to women to children, we at the HOT Report proudly welcome back the “come-back”…Penny Loafers! And surely you’ve seen the new Cole Haan Collection, including an adorable infant style.

Cleverly customary for both genders and viable with everything from a suit to jeans and even skirts, penny loafers have long made a smooth transition from power to play. The unique style of the vamp of the shoe that gives them their name has even been transplanted onto a high-heeled (and therefore non-loafer) version for today’s corporate denizens. Making the loafer chic and sophisticated!

When James Dean wore penny loafers with his by-then-standard white T-shirt and faded blue jeans in "Rebel Without a Cause," he changed the course of shoe history. Up to then, an entirely different kind of guy had worn what since has become a classic. The penny loafer was the shoe of choice for the conservative button-down-and-khakis set, who weren't exactly the "He's a Rebel" type. The penny loafer actually got its start (sans penny) 50 years ago, as the Weejun. In 1934 George Henry Bass (a bootmaker in Wilton, Maine) started making loafers and called them Weejuns (meant to sound like Norwegian). These had a strap across the upper part of the vamp that was shaped like a pair of lips (said to be John's wife, Alice Bass, kissing each shoe on its way out the door). The mouth opening soon was used to hold an ornament (such as a penny), and thus penny loafers became a style.

There’s no need to actually wear a penny inside your penny loafers. The style of this loafer is already unmistakable. But this year, Cole Haan has actually created a “special-kind-of-penny” to replace the “penny”. No penny required? This is 2008 and pennies really are somewhat passé, recall “penny candy?” The loafer however, whether tasseled or pennied will never retire. It is as classic as a Navy Blue Blazer or a LBD. This Fall and Winter, the shoe to own is the Classic Loafer (oxford, tasseled or pennied). Nearly every designer (Louboutin, Prada, Gucci, Michael Kors) and every major brand (Tod’s, Nine West, Bass) wants you to step into Fall with shiny new pennies in your shoes. And in most cases, pre-ordering is already underway. Don’t worry, this shoe runs the gamut of price points, so you should have plenty of spare change left to slip into your loafers. Now, that’s a come-back we can all appreciate!